How to Adjust to the Real World After College

How to Adjust to the Real World After College

This article first appeared in the Misseducated Substack. To get notified about when new articles come out, subscribe here.

Introduction

“Having the freedom to invent your life is a privilege.”[1]

“Do it—invent your life, in whatever form that ends up taking, which need not be very cool or glamorous or countercultural at all—for your own sake.”[2]

I have struggled to adjust to adult life after graduating from college, yet it’s something I rarely talk about with my friends. I attended competitive schools for my whole life, where I got used to the pressures of grades, internships, and fancy jobs. And yet now, 4 years out of university, the last thing I want to admit to my fellow college graduates is that I am not (yet) the young, instantly successful world leader that people had led me to believe I would be.

This article comes from a place of privilege, but also of deep irony: those of us who thrived in the world of academic achievement turn out to be very poorly adjusted for the open-ended uncertainty of “the real world”. As my high school history teacher, Dr. Ward-Smith, liked to put it:

“You are all poodles. And you’re very good at jumping through hoops.”

Without the safety net of school, many of us inevitably try to recreate that structure after college, falling into jobs at socially acceptable companies so that we can reassure ourselves, our parents, and our friends that yes, we’re still on the track of “success”. We move to the same cities. We take up the same safe jobs in banking or consulting or tech, with clear promotion tracks. It seems we will do anything to avoid looking in the mirror and facing the fact that it’s up to us to build our own lives now.

After college, I did exactly this. I had studied Business Analytics, which I pursued because it was intellectually stimulating but also “to keep the doors open”. Yet, it plonked me right in the middle of boring-yet-high-paying jobs. I wanted to be a dutiful employee, just like I had been a dutiful student. But I was no longer on the straight and linear path of grades. I was climbing on the jungle gym of a real-world career. And I was already miserable. The title of Marshall Goldsmith’s book echoed in my ears,

“What got you here won’t get you there.”[3]

The question then becomes, where are any of us going? How do you start to figure out who you are when you don’t even know what you want? And if you break away from the conveyor-belts of achievement, away from the privilege and praise imprisoning you, what on earth do you replace that with?

I don’t have all the answers, but I at least have thoughts on this topic that might help. Just to warn you, you probably shouldn’t listen to me; I have a lot less money than my peers who are still working their fancy jobs, albeit chained to their desks by golden handcuffs. I’m optimizing for having control of my time, which I’ll get into later.  

Tips

1.    Money and prestige alone will not make you happy

There is something masochistic about the world of top schools, jobs, and universities. They’re incredibly hard to get accepted into. They’re incredibly hard to stay in and excel in. It took me a lot of blood, tears, sweat and pain to get into Wharton. The Wharton core of Finance, Accounting and Statistics didn’t help at all. All these experiences primed me to have a ridiculous tolerance for doing things I hated doing. Fast forward, post-college, I spent three months trying to get a job, and took a role as Product Analyst at Postmates. I was using my data skills. I was making $100,000 a year, plus stock options. But something else happened that I could not have predicted: I was deeply, paralyzingly miserable.

I woke up every day dreading going to work. My work performance was average at best because of it. I hated that my boss told me what to do all day. I hated being compared to Sean (sorry, Sean), my boss’s team favorite. (As an aside, throughout my tech career, I have had more men called Sean on my teams than women.)

The thing about hating your cushy life is that people can tell. When you see family members and old friends at the holidays, and you’re dreading to tell them what you’re doing day-in-day-out, they will notice. You can see it in your friends, too, when they’re trying to convince themselves to stay in their role for another year to get that promotion.

It still blows my mind that the people with the most resources and the greatest safety-nets narrow themselves into jobs that make them actively hate their life. They seem to be the most dedicated to living a life that they think other people think they should be doing, but which ultimately isn’t their own.

Here’s a thought: You are privileged. You only get one life. Don’t spend it secretly hating it. If you’re unhappy, your boss or your parents aren’t going to fix that. It’s up to you to do something about it. Quit your job. Move to another city. Take a cooking course. Take the summer off, and work at the summer camp or resort you used to go to as a kid. It will help.

I didn’t learn my lesson from Postmates. Instead, I took essentially the same job at Vox Media and hated my life for another two years. Then, this summer, I worked at a small hotel in rural California, deep in the Tahoe National Forest, for $15 per hour. Minimum wage. My salary at Vox was closer to $60 per hour. Want to know something strange? I was happier cleaning toilets and chopping wood at the resort than doing data for Vox all day. I was poorer, and happier for it.

During this time, I was also rediscovering that what truly brings me joy is writing. Delighting my readers makes me so profoundly, deeply happy, even though I am yet to make a single cent from doing it. And I couldn’t care less. This time I’ve spent writing and making no money has been one of the happiest periods of my life.

The bottom line is that you don’t need more stuff, more titles, or a nicer apartment. You need to do things with your time that are meaningful to you, that enable you to become who you really are, and that serve others somehow in the process. If you don’t know what those are yet, never give up on trying to find them.

2.    Good mental health starts with being kind to yourself

We were raised during the self-esteem movement. Many of us were told our whole lives by our parents and our teachers how special, unique, and exceptional we were. For me, this manifested in me always needing to feel that I was better than other people in order to feel good about myself.

But it turns out this system set me up to fail in terms of my mental health. Out in the giant playing field of the real world, I’m not special. None of us are. What happens when we inevitably fail in our early years out of college, and don’t meet those ideal standards? What happens when we’re not Malala who got the Nobel Peace Prize at the age of 17? We feel lousy and terrible about ourselves. We’ve fallen short of everyone’s expectations. This can lead to…well…an overwhelming onset of self-criticism and depression, if not a colossal mental breakdown.

Luckily, Dr. Kristin Neff offers us another way forward. Neff has devoted her entire career to studying self-compassion and has made some profound discoveries in how it relates to self-esteem. In her TED Talk, which I’ve watched probably a hundred times, she says,

“How do we get off this treadmill, this constant need to feel better than others so that we can feel good about ourselves? That’s where self-compassion comes in.  Self-compassion is not about judging ourselves positively. Self-compassion is about relating to ourselves kindly, embracing ourselves as we are, flaws and all.”

At a high level, Neff suggests that when something bad happens to you, treat yourself with kindness like you would treat a good friend, with empathy, understanding and gentleness. Got a bad performance review at work? Give yourself a hug, say something soothing to yourself like, “It’s going to be okay. You’re going to get through this.” She reminds us that being imperfect is the central thing that unites us as human beings. She says,

“We make it so much worse for ourselves when we are isolated in our suffering and our imperfection, where in fact that’s precisely what connects us to other people.”

Self-compassion helps us build a sense of self-worth that is not about reaching some standard or judging ourselves positively, but because we are human beings and we are worthy of love and kindness.

3.    Have a spiritual awakening, or three

While getting a degree teaches us a lot, we end up absorbing a lot of the institution’s culture that we never signed up for. I loved writing and creating art when I was growing up. But when I turned 20, after spending 7 summers writing my first novel, I gave it up. I was attending The Wharton School. I was becoming a serious “business lady”. I didn’t have time for the frivolous pursuit of writing teen romance fiction. After Wharton, I’ve spent the rest of my 20s unlearning its ideas of what I should be doing with my life. It ended up taking me another 7 years to get back to the core of myself: someone with a ton of opinions with a love of other people’s stories that I want to amplify in the world.

How did I finally get back to who I was? Being too curious is probably the answer. In reality, that looked like a peyote ceremony, multiple psilocybin mushroom trips, and a bunch of trauma that came out of nowhere and subsequent therapy. So, if you really want to figure out who you are, buckle up for the ride! It’s going to be bumpy, but you won’t regret it.

There is one “spiritual-awakening-lite” I recommend that’s safe to try at home. Read The Artist’s Way by Julia Cameron and do the exercises. The book is over 30 years old, but it’s just as relevant as ever for those of us who need to tune in and unblock. The book relevant tool here is morning pages, or three pages of long-hand, stream-of-conscious journaling every day. If you don’t know what you want to do with your life, sitting down and doing your morning pages will whisper the next steps of your path to you. Just promise me that once you get your answers that you actually follow through and do them, okay?

4.    Listen for whispers of what you want, and then go after them

“Is there anything you’re interested in? Anything? Even a tiny bit? No matter how mundane or small?” “It might seem like nothing, but it’s a clue. Follow that clue. Trust it. See where curiosity will leave you next. Then follow the next clue, and the next, and the next.”[4]

Your passion, purpose, and a reason to live are not things that God will part the cloud to strike down on you from the sky. But if you’re doing your morning pages, and living with curiosity, you will start to get little hints of what is really inside of you, and what wants to come out of the shadows. Especially if you don’t know what you want, they start out in tiny little whispers. It could be as simple as:

  • “I loved picture book illustrations when I was a kid…”
  • “I’ve always wanted to go to Jakarta…”
  • “Charles Dickens has a house museum in London. I wonder where he got all his inspiration for his characters…”
  • “You know, Ethiopian food is pretty amazing. Could I make injera? There’s no way…”

Whatever comes to you will not be a clear or risk-free picture. But these are the clues. They are the next steps. And they are already within you. And what’s the point of living, if not with a little adventure?

In March 2022, I left New York City and spent some time upstate with a friend of mine who has shamanic tendencies. She held space for me in a mushroom ceremony, as I gushed to her about how stuck and unhappy I was in my life.  We were tucked away in her apartment, and a silent, late snow was falling outside. In the middle of the trip, I remember thinking about energy, and where my spirit was being called to live. I remembered that my spirit animal is the hummingbird.

“I need to live where hummingbirds live,” I cried out.

“Awesome, doll,” my friend said to me.

That was it. I knew in my heart what I had to do. Hummingbirds are native to the Americas, and my mother’s family is from California. Even before this mushroom trip, I had been getting a lot of energy from my long-dead great-grandmother, Hazel Sapero Weinberg. I later learnt that in Aztec mythology, hummingbirds represent the reincarnated souls of warriors and women who died in childbirth. Yes it’s crazy but moving to a place where I see hummingbirds regularly has been absolutely enlightening. I’ve mostly been in California and Mexico ever since. Do I know what I want to do after this? Heck no! But that doesn’t matter. As The Excellent Sheep says:

“Don’t try to figure out what you want to do with the rest of your life. You’re going to be a very different person in two or three years, and that person will have their own ideas. All you can really figure out is what you want to do right now.”[5]

One of the biggest benefits to being out of college is that, if you’re not inundated with work, you should have more free time to build your new identity and your new life. Many of my friends take up activities just for fun, including painting, pottery, volleyball, and triathlons. Taking time to play games and be creative is great for feeding your soul, as long as you are not secretly using them to continue to show off to other people how accomplished and amazing you are.

Just as you’re pursuing creative hobbies, get creative about the different types of lives that you could live. If you know you have an interest in medicine, but aren’t sure which path to go down, try creating a series of options for your life that sound exciting to you. For example, you could become a pathologist, you could become a medical writer for a news publication, or you could get a degree and join Doctors Without Borders to help people around the world. There are multiple, different, fascinating, awesome lives that each of us could be living. And if you try pursuing one of them and it doesn’t work out, you can always try something else.

5.    Make new friends

I have struggled to make new friends since I’m no longer on a campus with everyone I know and love living within a 15 minutes’ walk away. But two things are true: I absolutely love my friends from college, and I would be a far more stagnated person if I had only hung out with Penn people in the last 4 years since I’ve graduated.

In the adult world, the best way I’ve found to make new friends is to join communities organized around an activity you want to do or an interest you want to develop. I know, this sounds boring and it will feel like manufactured friendship the first number of times you hang out. But it is a great way to reorganize your life into the self who you are working to uncover. I joined a number of virtual writing communities, as well as tech freelancing groups. From these, I’ve developed in-person and virtual friendships with people from all different kinds of life stages.  

An extreme example of this as a forcing function is to move to a new city where you don’t really know anyone. From this you’ll gain all new coworkers and group hangouts. Yet I have found that meeting adults of different ages is incredibly grounding. It’s eye-opening to realize that there are literally endless, awesome ways to live and still thrive as an adult. Each of us still has so much more to learn.

6.    If you want to make a change in your life, do it now.

The tough reality of adult life is that no one is coming to save you. You’re the only one steering this ship of your life. If you are unhappy, it’s up to you to plan for when you are going to change. In my personal experience, when I was paralyzed by fear, I set my date of change way into the distant future. For example, back in March 2022 when I sat for that mushroom ceremony, I was sick of living in Williamsburg because it was so expensive. I had been waking up for over a year hating my life every day and feeling completely stuck. Yet I told myself:

I’ll just wait until October 2022 when my lease is up. Even though I’m so miserable, I’ve got to hang in there.

I told my friend about my predicament,

“I can’t do anything about it until October.”

“Why not?” she asked.

“That’s when my lease ends.”

“But you don’t have to live there. Those housemates, they’re not even your friends.”

For the first time in a really long time, I listened. I didn’t need to live in my apartment. I didn’t need to keep going with this job that I hated. I ended up quitting that very next day (after the mushroom ceremony) and finding a subletter. So instead, in these six months, I became a full-time writer (!), travelled a ton in Mexico and California (!), finished writing my first novel (!) and relaunched my blog and Substack (!). I am finally living the life that I want, for now, and staying true to that.

So, if you want to make a change in your life, set a date. Then find the day 6 months earlier than that date. Mark this in your calendar, “Deadline for Change.”

When we are living lives that aren’t right for us, when we are really stuck in a dark corner and our self-worth is really low, and we can’t see any better way forwards, it is so hard to snap out of it. It’s hard to imagine that you deserve better, that you deserve to put an end to your misery and make a change. For me, part of this had to do with sunk costs.

I’ve been doing this job for two years and I’ve been miserable. Why do I deserve any better? What’s different about today?

Because everything is different today. Today you don’t have another second to waste living a life that makes you miserable. Today is the day you deserve to wake up building a life that is really awesome and stop putting yourself through hell. You don’t have another six months to waste before you start to make changes. You are not going to resign yourself to a life that you hate. Instead, you are going to take deliberate action to change all this. But before you do that, you’ll need one more thing…

7.    Courage is the most important of all the virtues

“Courage is the most important of all the virtues,” said Maya Angelou, “Because without courage, you can’t practice any other virtue consistently.”

I knew for ages that I needed to quit my job. But I felt scared and stuck. I didn’t know where I was going to live or what I was going to do. And so to make any kind of drastic change in life, I needed a lot of courage. It’s put well in The Excellent Sheep:

“If you aren’t giving anything up, it isn’t moral and it isn’t courage. Stumbles, sacrifices, inner struggle, false starts and wrong turns, conflict with parents and peers…The way you know it’s real is if it hurts.”[6]

In moments when you are terrified of exploring new jobs, a new version of yourself, a new hobby, a new life, call deep on your courage. You will fail. It is inevitable. The point is, do you have the courage and the perseverance to keep going, to keep building a life that is better for yourself? Will you take yourself with you, and live to the fullest? Or will you stay the safe course and go gently into that good night?

8.    Remember that your corporation does not give a fuck about you  

I was fired from my first job out of college. It had taken me 3 months to get the job in the first place. Only 8 months later, my boss and Stephanie from HR pulled me into a random room with no windows on a Friday morning and told me that I was “no longer a fit.” I didn’t even reach my 1-year equity cliff, where I would have received around 1,200 shares that I had negotiated diligently as part of my offer. My cushy tech job was not as cush as I arrogantly blabbed about to everyone. I remember sitting across from my manager, too livid to cry, as Stephanie put a booklet on the table in front of me. It was the employee contract I had signed only a few months before.

“Hire and fire at will” are the only words that I remember now.

I have a lot of very hard-working friends who devote much of their lives to their corporations. These corporations themselves speak of the “family” environments, the off-sites, the happy-hours, and how much they value you. While this may be well-intended, it is ultimately bullshit. You are not that important to them. Your work is not that important to them, otherwise they would pay you a lot more for it. If they decided to fire you tomorrow, they could replace you very easily. Too easily, in fact. When I left my jobs, the Seans on my teams quickly rose to the occasion.

Your employer is not your teacher. Your employer is not your parent. Given a rocky quarter, or a restructuring, or an executive’s brain fart, they will fire you. This is not to scare you. It’s just to say that you should not be naïve about this. It is a transactional relationship. The corporation exchanges your work for money, until it no longer suits them for any reason, and they will burn you out in the process if it benefits them. But deep down, you know things that the corporation does not.

Your life is not expendable. Your time matters. Your life is worth something. There are so many ways you could be living your life. You could be leading 5-day hikes in Iceland. You could be the pastor of your local parish church. You could be embroidering quilts to sell on Etsy. So, you need to advocate for yourself and make working at this corporation worthwhile for you.

Have you taken your vacation days? Have you asked about a pay raise, or a sabbatical, or a 4-day work week, or compensation for relocating, or working remotely, or getting new computer gear? Have you asked about getting staffed on that project that you wanted, so you could learn about a new part of the industry?

At Vox Media, I was working with humans, but ultimately the corporation was a legal entity. My real job there was to advocate for career advancements that mattered to me, and milk the legal entity for everything that it was worth, which I did the entire two years I was there. Every quarter I asked my boss if I could become a Product Manager (I was still under the illusion that this title would have made me more palatable to myself and other people). When they didn’t offer me that, I finally quit.

These corporate legal entities benefit from the fact that we are overworked and have no time to develop our own identities and interests outside of the walls of their (virtual) offices. Unless we have the courage to make change, these legal entities continue to benefit from the fact that we have no idea who we are. They will keep us on the path that they have set out for us. They will do whatever makes sense for their bottom line.

9.    Do not care about what other people think of you

“Many people are living lives that they don’t really want to be living. They’re doing things they don’t really want to be doing. They are in relationships they don’t really want to be in because they care what other people think. You will never live the life you truly want to live if you care about what other people think, and you will never be truly happy if you care about what other people think.” Cindy Gallop, Design Matters Podcast.

I felt a lot of this pressure before. Since graduating, I lived in New York and San Francisco because I cared what other people thought. When I met someone at an event or a party, and they asked me questions about myself, I wanted to be palatable to them. In fact, one of my deepest insecurities is that I wanted people to believe that I was intelligent.

This insecurity goes far back into my early childhood. Why did I have this analytics job? Oh yeah, I wanted Barry Nix and my dad to respect me. I’m a woman. Doing a job in statistics would help them see that I’m intelligent enough. These thoughts of mine, though true, were old. And yet they had stuck with me for all these decades. I knew that they came from a pure place originally when I was a child and we went to visit the Nix’s mansion in the English countryside. My dad and Barry Nix had worked together at Bear Stearns, a company that no longer exists because of its toxic culture, dripping like poison, and its malevolent practices. My dad would sit with Barry and their friends’ watching sports and drinking wine in front of a large TV, while the women would stand in the kitchen and obviously be talking about something as stereotypical as childcare.

I had decided then and there that I wanted to be one of the men. And again, the pure place inside of me had the right idea, it just came out wrong. Years of analytics jobs that I detested later, I broke this revelation to my career coach, Robin.

“I just want people to think I’m smart and I’m intelligent enough,” I said to her.

“You can’t control what they think,” Robin said, obviously concerned that this was our third conversation and I’d made no change so far, “And why does it have to be statistics? Aren’t writers and artists intelligent people?”

She had a point. In fact, why did I still care what Barry Nix thought? I hadn’t seen the man in 15 years.

As Elizabeth Gilbert says in Big Magic,

“Nobody’s thinking about you…People are mostly just thinking about themselves… Go be whomever you want to be, then. Do whatever you want to do. Pursue whatever fascinates you and bring you to life. Create what you want to create—and let it be stupendously imperfect, because it’s exceedingly likely that nobody will even notice. And that’s awesome.”[7]

This perspective is freeing. Life is short. We are going to be dead soon, and people who are older than us that we look up to will most likely be dead sooner. It makes no sense to continue to craft our lives around our child-like interpretations of how we can gain their love, their approval, and their affection.

10.    Do something generous

Another bad outcome of the self-esteem movement is that for a long time I suffered from terrible career anxiety. I was overwhelmingly concerned with my success, and my success alone. This approach to life is not only incredibly selfish, but incredibly lonely. Luckily, Seth Godin has a helpful response to this:

“Anxiety is experiencing failure in advance…The question is how do we focus that part of our attention on something generous instead, because anxiety and worry is almost never in service of someone else.”

The insecure, success-hungry part of myself felt permanently stressed, scared, and starved of attention and praise. But on brief days when I could turn my energy away from myself and outwards towards helping someone else, things suddenly became exciting and meaningful. I get excited about writing something that will help other people. I’m writing this piece because my friend requested it. It’s why I wanted to build Misseducated in the first place. And by god, delighting even one reader has made it all worth it.

In her TED Talk, another one of my personal faves, Cambridge University researcher Olivia Remes talks about this exact thing,

“Whatever we do in life, whatever work we produce, however much money we make, we cannot be fully happy until we know that someone else needs us, that someone else depends on our accomplishments…but if we don’t do something with someone else in mind, then we’re at much higher risk for poor mental health.”

So, have you done something with someone else in mind today? Is there a project you’ve been meaning to do to help someone but you haven’t started yet? Get on it! That will save you from the tyranny of your deprived, no-longer-graded self.

11.    Ditch reassurance. Embrace the fact that this might not work

In university I received an ungodly amount of praise. On every paper I wrote, in every class I participated in, I craved yet more approval from my professors.

“Excellent essay Natasha…”

“That is such a good question…”

Entering the real world was a slap in the face in that sense. But to live a healthy adult life, where I would take risks and try out jobs and fail and learn, I realized that I had to cut myself off from this lifeline of approval and try things that were different. As Seth Godin puts it,

“The alternative is to say this might not work. This thing I did, this thing I cared about might not work. Odds are it won’t, but I have a portfolio and then I’ll make the next thing because we don’t live on the savannah. This is not a matter of life or death most of the time. It is instead a matter of ego and self-esteem, and it’s not fatal. All of the worrying is worse than the rejection when it finally comes.”

This point is more important than it first appears. We have to take risks. We have to make mistakes. We have step away from what The Excellent Sheep describes as “credentialism”, where “the purpose of life becomes the accumulation of gold stars.”[8] Once we can do that, we can pursue something for the simple fact that it will probably fail, but it might help someone, and we might learn something in the process. Then, I guarantee, fun, experimentalism, curiosity, play, excitement, growth, and wonder are waiting for us on the other side.

Conclusion

“The reason to try, the reason to invent your life—whether you aim at remarkable things or only at your own thing—is so that it will be your life, your choice, your mistakes.”[9]

At the end of the day, we are all going to die. Sorry to be so morbid, but in 100 years from now, everyone that you know will most likely not be alive. This is just to say that you only get one life. It takes time and lots of trial and error to craft and curate the life that you really want. But this is perhaps the most important thing that any of us will be called to do. To be able to say that we lived the one life that we were given well. That we helped others. That we spent it doing something worthwhile. That is something that goes far beyond the praise, the achievements, the fancy titles, the salaries, and the approval of our status-driven institutions.

This endeavor takes courage. It takes deep reflection. It takes self-discovery. And it also takes learning a thing or two about your values. It is not too late. It is never too late. There are women in their 80s in my writing class who are just starting their memoirs, and it’s been amazing to hear their stories. Our stories matter. Our time matters. It’s up to us to dig deep, and figure out who we are, so that we can show up as our best selves in the world. So that we can create our best things. So that we can do our best work.

I’ll leave you with some parting words of wisdom from Cindy Gallop on the importance of discovering our values:

“Look into yourself, and identify who you are, what you stand for, what you believe in, what you value. Decide what your values are, and then operate accordingly to them. And when you do that, it makes life so much easier, because life will give you all the same shit it always will, but you’ll know exactly how to respond to it at any given situation in a way that is true to you. That way you are only ever operating for things that are true to you. And that is what matters, not what other people think.”

So, figure out who you are. Have the courage to keep trying, keep failing, keep testing and keep going. And live a life in accordance with your values that you can be proud of.

Many thanks to Alara Gebes for requesting this article, and to Deniz Kecik and Alan Jinich for their feedback.

If you enjoyed this article, please consider subscribing to the Misseducated Substack.

References

[1] Deresiewicz, W. (2014). Excellent sheep: The miseducation of the American elite and the way to a meaningful life.
[2] Ibid.
[3] Goldsmith, M., & Reiter, M. (2007). What got you here won't get you there: how successful people become even more successful. New York, NY, Hyperion.
[4] Gilbert, E., 2016. Big Magic: Bloomsbury Publishing.
[5]  Deresiewicz, W. (2014). Excellent sheep: The miseducation of the American elite and the way to a meaningful life.
[6] Ibid.
[7] Gilbert, E., 2016. Big Magic: Bloomsbury Publishing.
[8] Deresiewicz, W. (2014). Excellent sheep: The miseducation of the American elite and the way to a meaningful life.
[9] Ibid.

How to Adjust to the Real World After College

This article first appeared in the Misseducated Substack. To get notified about when new articles come out, subscribe here.

Introduction

“Having the freedom to invent your life is a privilege.”[1]

“Do it—invent your life, in whatever form that ends up taking, which need not be very cool or glamorous or countercultural at all—for your own sake.”[2]

I have struggled to adjust to adult life after graduating from college, yet it’s something I rarely talk about with my friends. I attended competitive schools for my whole life, where I got used to the pressures of grades, internships, and fancy jobs. And yet now, 4 years out of university, the last thing I want to admit to my fellow college graduates is that I am not (yet) the young, instantly successful world leader that people had led me to believe I would be.

This article comes from a place of privilege, but also of deep irony: those of us who thrived in the world of academic achievement turn out to be very poorly adjusted for the open-ended uncertainty of “the real world”. As my high school history teacher, Dr. Ward-Smith, liked to put it:

“You are all poodles. And you’re very good at jumping through hoops.”

Without the safety net of school, many of us inevitably try to recreate that structure after college, falling into jobs at socially acceptable companies so that we can reassure ourselves, our parents, and our friends that yes, we’re still on the track of “success”. We move to the same cities. We take up the same safe jobs in banking or consulting or tech, with clear promotion tracks. It seems we will do anything to avoid looking in the mirror and facing the fact that it’s up to us to build our own lives now.

After college, I did exactly this. I had studied Business Analytics, which I pursued because it was intellectually stimulating but also “to keep the doors open”. Yet, it plonked me right in the middle of boring-yet-high-paying jobs. I wanted to be a dutiful employee, just like I had been a dutiful student. But I was no longer on the straight and linear path of grades. I was climbing on the jungle gym of a real-world career. And I was already miserable. The title of Marshall Goldsmith’s book echoed in my ears,

“What got you here won’t get you there.”[3]

The question then becomes, where are any of us going? How do you start to figure out who you are when you don’t even know what you want? And if you break away from the conveyor-belts of achievement, away from the privilege and praise imprisoning you, what on earth do you replace that with?

I don’t have all the answers, but I at least have thoughts on this topic that might help. Just to warn you, you probably shouldn’t listen to me; I have a lot less money than my peers who are still working their fancy jobs, albeit chained to their desks by golden handcuffs. I’m optimizing for having control of my time, which I’ll get into later.  

Tips

1.    Money and prestige alone will not make you happy

There is something masochistic about the world of top schools, jobs, and universities. They’re incredibly hard to get accepted into. They’re incredibly hard to stay in and excel in. It took me a lot of blood, tears, sweat and pain to get into Wharton. The Wharton core of Finance, Accounting and Statistics didn’t help at all. All these experiences primed me to have a ridiculous tolerance for doing things I hated doing. Fast forward, post-college, I spent three months trying to get a job, and took a role as Product Analyst at Postmates. I was using my data skills. I was making $100,000 a year, plus stock options. But something else happened that I could not have predicted: I was deeply, paralyzingly miserable.

I woke up every day dreading going to work. My work performance was average at best because of it. I hated that my boss told me what to do all day. I hated being compared to Sean (sorry, Sean), my boss’s team favorite. (As an aside, throughout my tech career, I have had more men called Sean on my teams than women.)

The thing about hating your cushy life is that people can tell. When you see family members and old friends at the holidays, and you’re dreading to tell them what you’re doing day-in-day-out, they will notice. You can see it in your friends, too, when they’re trying to convince themselves to stay in their role for another year to get that promotion.

It still blows my mind that the people with the most resources and the greatest safety-nets narrow themselves into jobs that make them actively hate their life. They seem to be the most dedicated to living a life that they think other people think they should be doing, but which ultimately isn’t their own.

Here’s a thought: You are privileged. You only get one life. Don’t spend it secretly hating it. If you’re unhappy, your boss or your parents aren’t going to fix that. It’s up to you to do something about it. Quit your job. Move to another city. Take a cooking course. Take the summer off, and work at the summer camp or resort you used to go to as a kid. It will help.

I didn’t learn my lesson from Postmates. Instead, I took essentially the same job at Vox Media and hated my life for another two years. Then, this summer, I worked at a small hotel in rural California, deep in the Tahoe National Forest, for $15 per hour. Minimum wage. My salary at Vox was closer to $60 per hour. Want to know something strange? I was happier cleaning toilets and chopping wood at the resort than doing data for Vox all day. I was poorer, and happier for it.

During this time, I was also rediscovering that what truly brings me joy is writing. Delighting my readers makes me so profoundly, deeply happy, even though I am yet to make a single cent from doing it. And I couldn’t care less. This time I’ve spent writing and making no money has been one of the happiest periods of my life.

The bottom line is that you don’t need more stuff, more titles, or a nicer apartment. You need to do things with your time that are meaningful to you, that enable you to become who you really are, and that serve others somehow in the process. If you don’t know what those are yet, never give up on trying to find them.

2.    Good mental health starts with being kind to yourself

We were raised during the self-esteem movement. Many of us were told our whole lives by our parents and our teachers how special, unique, and exceptional we were. For me, this manifested in me always needing to feel that I was better than other people in order to feel good about myself.

But it turns out this system set me up to fail in terms of my mental health. Out in the giant playing field of the real world, I’m not special. None of us are. What happens when we inevitably fail in our early years out of college, and don’t meet those ideal standards? What happens when we’re not Malala who got the Nobel Peace Prize at the age of 17? We feel lousy and terrible about ourselves. We’ve fallen short of everyone’s expectations. This can lead to…well…an overwhelming onset of self-criticism and depression, if not a colossal mental breakdown.

Luckily, Dr. Kristin Neff offers us another way forward. Neff has devoted her entire career to studying self-compassion and has made some profound discoveries in how it relates to self-esteem. In her TED Talk, which I’ve watched probably a hundred times, she says,

“How do we get off this treadmill, this constant need to feel better than others so that we can feel good about ourselves? That’s where self-compassion comes in.  Self-compassion is not about judging ourselves positively. Self-compassion is about relating to ourselves kindly, embracing ourselves as we are, flaws and all.”

At a high level, Neff suggests that when something bad happens to you, treat yourself with kindness like you would treat a good friend, with empathy, understanding and gentleness. Got a bad performance review at work? Give yourself a hug, say something soothing to yourself like, “It’s going to be okay. You’re going to get through this.” She reminds us that being imperfect is the central thing that unites us as human beings. She says,

“We make it so much worse for ourselves when we are isolated in our suffering and our imperfection, where in fact that’s precisely what connects us to other people.”

Self-compassion helps us build a sense of self-worth that is not about reaching some standard or judging ourselves positively, but because we are human beings and we are worthy of love and kindness.

3.    Have a spiritual awakening, or three

While getting a degree teaches us a lot, we end up absorbing a lot of the institution’s culture that we never signed up for. I loved writing and creating art when I was growing up. But when I turned 20, after spending 7 summers writing my first novel, I gave it up. I was attending The Wharton School. I was becoming a serious “business lady”. I didn’t have time for the frivolous pursuit of writing teen romance fiction. After Wharton, I’ve spent the rest of my 20s unlearning its ideas of what I should be doing with my life. It ended up taking me another 7 years to get back to the core of myself: someone with a ton of opinions with a love of other people’s stories that I want to amplify in the world.

How did I finally get back to who I was? Being too curious is probably the answer. In reality, that looked like a peyote ceremony, multiple psilocybin mushroom trips, and a bunch of trauma that came out of nowhere and subsequent therapy. So, if you really want to figure out who you are, buckle up for the ride! It’s going to be bumpy, but you won’t regret it.

There is one “spiritual-awakening-lite” I recommend that’s safe to try at home. Read The Artist’s Way by Julia Cameron and do the exercises. The book is over 30 years old, but it’s just as relevant as ever for those of us who need to tune in and unblock. The book relevant tool here is morning pages, or three pages of long-hand, stream-of-conscious journaling every day. If you don’t know what you want to do with your life, sitting down and doing your morning pages will whisper the next steps of your path to you. Just promise me that once you get your answers that you actually follow through and do them, okay?

4.    Listen for whispers of what you want, and then go after them

“Is there anything you’re interested in? Anything? Even a tiny bit? No matter how mundane or small?” “It might seem like nothing, but it’s a clue. Follow that clue. Trust it. See where curiosity will leave you next. Then follow the next clue, and the next, and the next.”[4]

Your passion, purpose, and a reason to live are not things that God will part the cloud to strike down on you from the sky. But if you’re doing your morning pages, and living with curiosity, you will start to get little hints of what is really inside of you, and what wants to come out of the shadows. Especially if you don’t know what you want, they start out in tiny little whispers. It could be as simple as:

  • “I loved picture book illustrations when I was a kid…”
  • “I’ve always wanted to go to Jakarta…”
  • “Charles Dickens has a house museum in London. I wonder where he got all his inspiration for his characters…”
  • “You know, Ethiopian food is pretty amazing. Could I make injera? There’s no way…”

Whatever comes to you will not be a clear or risk-free picture. But these are the clues. They are the next steps. And they are already within you. And what’s the point of living, if not with a little adventure?

In March 2022, I left New York City and spent some time upstate with a friend of mine who has shamanic tendencies. She held space for me in a mushroom ceremony, as I gushed to her about how stuck and unhappy I was in my life.  We were tucked away in her apartment, and a silent, late snow was falling outside. In the middle of the trip, I remember thinking about energy, and where my spirit was being called to live. I remembered that my spirit animal is the hummingbird.

“I need to live where hummingbirds live,” I cried out.

“Awesome, doll,” my friend said to me.

That was it. I knew in my heart what I had to do. Hummingbirds are native to the Americas, and my mother’s family is from California. Even before this mushroom trip, I had been getting a lot of energy from my long-dead great-grandmother, Hazel Sapero Weinberg. I later learnt that in Aztec mythology, hummingbirds represent the reincarnated souls of warriors and women who died in childbirth. Yes it’s crazy but moving to a place where I see hummingbirds regularly has been absolutely enlightening. I’ve mostly been in California and Mexico ever since. Do I know what I want to do after this? Heck no! But that doesn’t matter. As The Excellent Sheep says:

“Don’t try to figure out what you want to do with the rest of your life. You’re going to be a very different person in two or three years, and that person will have their own ideas. All you can really figure out is what you want to do right now.”[5]

One of the biggest benefits to being out of college is that, if you’re not inundated with work, you should have more free time to build your new identity and your new life. Many of my friends take up activities just for fun, including painting, pottery, volleyball, and triathlons. Taking time to play games and be creative is great for feeding your soul, as long as you are not secretly using them to continue to show off to other people how accomplished and amazing you are.

Just as you’re pursuing creative hobbies, get creative about the different types of lives that you could live. If you know you have an interest in medicine, but aren’t sure which path to go down, try creating a series of options for your life that sound exciting to you. For example, you could become a pathologist, you could become a medical writer for a news publication, or you could get a degree and join Doctors Without Borders to help people around the world. There are multiple, different, fascinating, awesome lives that each of us could be living. And if you try pursuing one of them and it doesn’t work out, you can always try something else.

5.    Make new friends

I have struggled to make new friends since I’m no longer on a campus with everyone I know and love living within a 15 minutes’ walk away. But two things are true: I absolutely love my friends from college, and I would be a far more stagnated person if I had only hung out with Penn people in the last 4 years since I’ve graduated.

In the adult world, the best way I’ve found to make new friends is to join communities organized around an activity you want to do or an interest you want to develop. I know, this sounds boring and it will feel like manufactured friendship the first number of times you hang out. But it is a great way to reorganize your life into the self who you are working to uncover. I joined a number of virtual writing communities, as well as tech freelancing groups. From these, I’ve developed in-person and virtual friendships with people from all different kinds of life stages.  

An extreme example of this as a forcing function is to move to a new city where you don’t really know anyone. From this you’ll gain all new coworkers and group hangouts. Yet I have found that meeting adults of different ages is incredibly grounding. It’s eye-opening to realize that there are literally endless, awesome ways to live and still thrive as an adult. Each of us still has so much more to learn.

6.    If you want to make a change in your life, do it now.

The tough reality of adult life is that no one is coming to save you. You’re the only one steering this ship of your life. If you are unhappy, it’s up to you to plan for when you are going to change. In my personal experience, when I was paralyzed by fear, I set my date of change way into the distant future. For example, back in March 2022 when I sat for that mushroom ceremony, I was sick of living in Williamsburg because it was so expensive. I had been waking up for over a year hating my life every day and feeling completely stuck. Yet I told myself:

I’ll just wait until October 2022 when my lease is up. Even though I’m so miserable, I’ve got to hang in there.

I told my friend about my predicament,

“I can’t do anything about it until October.”

“Why not?” she asked.

“That’s when my lease ends.”

“But you don’t have to live there. Those housemates, they’re not even your friends.”

For the first time in a really long time, I listened. I didn’t need to live in my apartment. I didn’t need to keep going with this job that I hated. I ended up quitting that very next day (after the mushroom ceremony) and finding a subletter. So instead, in these six months, I became a full-time writer (!), travelled a ton in Mexico and California (!), finished writing my first novel (!) and relaunched my blog and Substack (!). I am finally living the life that I want, for now, and staying true to that.

So, if you want to make a change in your life, set a date. Then find the day 6 months earlier than that date. Mark this in your calendar, “Deadline for Change.”

When we are living lives that aren’t right for us, when we are really stuck in a dark corner and our self-worth is really low, and we can’t see any better way forwards, it is so hard to snap out of it. It’s hard to imagine that you deserve better, that you deserve to put an end to your misery and make a change. For me, part of this had to do with sunk costs.

I’ve been doing this job for two years and I’ve been miserable. Why do I deserve any better? What’s different about today?

Because everything is different today. Today you don’t have another second to waste living a life that makes you miserable. Today is the day you deserve to wake up building a life that is really awesome and stop putting yourself through hell. You don’t have another six months to waste before you start to make changes. You are not going to resign yourself to a life that you hate. Instead, you are going to take deliberate action to change all this. But before you do that, you’ll need one more thing…

7.    Courage is the most important of all the virtues

“Courage is the most important of all the virtues,” said Maya Angelou, “Because without courage, you can’t practice any other virtue consistently.”

I knew for ages that I needed to quit my job. But I felt scared and stuck. I didn’t know where I was going to live or what I was going to do. And so to make any kind of drastic change in life, I needed a lot of courage. It’s put well in The Excellent Sheep:

“If you aren’t giving anything up, it isn’t moral and it isn’t courage. Stumbles, sacrifices, inner struggle, false starts and wrong turns, conflict with parents and peers…The way you know it’s real is if it hurts.”[6]

In moments when you are terrified of exploring new jobs, a new version of yourself, a new hobby, a new life, call deep on your courage. You will fail. It is inevitable. The point is, do you have the courage and the perseverance to keep going, to keep building a life that is better for yourself? Will you take yourself with you, and live to the fullest? Or will you stay the safe course and go gently into that good night?

8.    Remember that your corporation does not give a fuck about you  

I was fired from my first job out of college. It had taken me 3 months to get the job in the first place. Only 8 months later, my boss and Stephanie from HR pulled me into a random room with no windows on a Friday morning and told me that I was “no longer a fit.” I didn’t even reach my 1-year equity cliff, where I would have received around 1,200 shares that I had negotiated diligently as part of my offer. My cushy tech job was not as cush as I arrogantly blabbed about to everyone. I remember sitting across from my manager, too livid to cry, as Stephanie put a booklet on the table in front of me. It was the employee contract I had signed only a few months before.

“Hire and fire at will” are the only words that I remember now.

I have a lot of very hard-working friends who devote much of their lives to their corporations. These corporations themselves speak of the “family” environments, the off-sites, the happy-hours, and how much they value you. While this may be well-intended, it is ultimately bullshit. You are not that important to them. Your work is not that important to them, otherwise they would pay you a lot more for it. If they decided to fire you tomorrow, they could replace you very easily. Too easily, in fact. When I left my jobs, the Seans on my teams quickly rose to the occasion.

Your employer is not your teacher. Your employer is not your parent. Given a rocky quarter, or a restructuring, or an executive’s brain fart, they will fire you. This is not to scare you. It’s just to say that you should not be naïve about this. It is a transactional relationship. The corporation exchanges your work for money, until it no longer suits them for any reason, and they will burn you out in the process if it benefits them. But deep down, you know things that the corporation does not.

Your life is not expendable. Your time matters. Your life is worth something. There are so many ways you could be living your life. You could be leading 5-day hikes in Iceland. You could be the pastor of your local parish church. You could be embroidering quilts to sell on Etsy. So, you need to advocate for yourself and make working at this corporation worthwhile for you.

Have you taken your vacation days? Have you asked about a pay raise, or a sabbatical, or a 4-day work week, or compensation for relocating, or working remotely, or getting new computer gear? Have you asked about getting staffed on that project that you wanted, so you could learn about a new part of the industry?

At Vox Media, I was working with humans, but ultimately the corporation was a legal entity. My real job there was to advocate for career advancements that mattered to me, and milk the legal entity for everything that it was worth, which I did the entire two years I was there. Every quarter I asked my boss if I could become a Product Manager (I was still under the illusion that this title would have made me more palatable to myself and other people). When they didn’t offer me that, I finally quit.

These corporate legal entities benefit from the fact that we are overworked and have no time to develop our own identities and interests outside of the walls of their (virtual) offices. Unless we have the courage to make change, these legal entities continue to benefit from the fact that we have no idea who we are. They will keep us on the path that they have set out for us. They will do whatever makes sense for their bottom line.

9.    Do not care about what other people think of you

“Many people are living lives that they don’t really want to be living. They’re doing things they don’t really want to be doing. They are in relationships they don’t really want to be in because they care what other people think. You will never live the life you truly want to live if you care about what other people think, and you will never be truly happy if you care about what other people think.” Cindy Gallop, Design Matters Podcast.

I felt a lot of this pressure before. Since graduating, I lived in New York and San Francisco because I cared what other people thought. When I met someone at an event or a party, and they asked me questions about myself, I wanted to be palatable to them. In fact, one of my deepest insecurities is that I wanted people to believe that I was intelligent.

This insecurity goes far back into my early childhood. Why did I have this analytics job? Oh yeah, I wanted Barry Nix and my dad to respect me. I’m a woman. Doing a job in statistics would help them see that I’m intelligent enough. These thoughts of mine, though true, were old. And yet they had stuck with me for all these decades. I knew that they came from a pure place originally when I was a child and we went to visit the Nix’s mansion in the English countryside. My dad and Barry Nix had worked together at Bear Stearns, a company that no longer exists because of its toxic culture, dripping like poison, and its malevolent practices. My dad would sit with Barry and their friends’ watching sports and drinking wine in front of a large TV, while the women would stand in the kitchen and obviously be talking about something as stereotypical as childcare.

I had decided then and there that I wanted to be one of the men. And again, the pure place inside of me had the right idea, it just came out wrong. Years of analytics jobs that I detested later, I broke this revelation to my career coach, Robin.

“I just want people to think I’m smart and I’m intelligent enough,” I said to her.

“You can’t control what they think,” Robin said, obviously concerned that this was our third conversation and I’d made no change so far, “And why does it have to be statistics? Aren’t writers and artists intelligent people?”

She had a point. In fact, why did I still care what Barry Nix thought? I hadn’t seen the man in 15 years.

As Elizabeth Gilbert says in Big Magic,

“Nobody’s thinking about you…People are mostly just thinking about themselves… Go be whomever you want to be, then. Do whatever you want to do. Pursue whatever fascinates you and bring you to life. Create what you want to create—and let it be stupendously imperfect, because it’s exceedingly likely that nobody will even notice. And that’s awesome.”[7]

This perspective is freeing. Life is short. We are going to be dead soon, and people who are older than us that we look up to will most likely be dead sooner. It makes no sense to continue to craft our lives around our child-like interpretations of how we can gain their love, their approval, and their affection.

10.    Do something generous

Another bad outcome of the self-esteem movement is that for a long time I suffered from terrible career anxiety. I was overwhelmingly concerned with my success, and my success alone. This approach to life is not only incredibly selfish, but incredibly lonely. Luckily, Seth Godin has a helpful response to this:

“Anxiety is experiencing failure in advance…The question is how do we focus that part of our attention on something generous instead, because anxiety and worry is almost never in service of someone else.”

The insecure, success-hungry part of myself felt permanently stressed, scared, and starved of attention and praise. But on brief days when I could turn my energy away from myself and outwards towards helping someone else, things suddenly became exciting and meaningful. I get excited about writing something that will help other people. I’m writing this piece because my friend requested it. It’s why I wanted to build Misseducated in the first place. And by god, delighting even one reader has made it all worth it.

In her TED Talk, another one of my personal faves, Cambridge University researcher Olivia Remes talks about this exact thing,

“Whatever we do in life, whatever work we produce, however much money we make, we cannot be fully happy until we know that someone else needs us, that someone else depends on our accomplishments…but if we don’t do something with someone else in mind, then we’re at much higher risk for poor mental health.”

So, have you done something with someone else in mind today? Is there a project you’ve been meaning to do to help someone but you haven’t started yet? Get on it! That will save you from the tyranny of your deprived, no-longer-graded self.

11.    Ditch reassurance. Embrace the fact that this might not work

In university I received an ungodly amount of praise. On every paper I wrote, in every class I participated in, I craved yet more approval from my professors.

“Excellent essay Natasha…”

“That is such a good question…”

Entering the real world was a slap in the face in that sense. But to live a healthy adult life, where I would take risks and try out jobs and fail and learn, I realized that I had to cut myself off from this lifeline of approval and try things that were different. As Seth Godin puts it,

“The alternative is to say this might not work. This thing I did, this thing I cared about might not work. Odds are it won’t, but I have a portfolio and then I’ll make the next thing because we don’t live on the savannah. This is not a matter of life or death most of the time. It is instead a matter of ego and self-esteem, and it’s not fatal. All of the worrying is worse than the rejection when it finally comes.”

This point is more important than it first appears. We have to take risks. We have to make mistakes. We have step away from what The Excellent Sheep describes as “credentialism”, where “the purpose of life becomes the accumulation of gold stars.”[8] Once we can do that, we can pursue something for the simple fact that it will probably fail, but it might help someone, and we might learn something in the process. Then, I guarantee, fun, experimentalism, curiosity, play, excitement, growth, and wonder are waiting for us on the other side.

Conclusion

“The reason to try, the reason to invent your life—whether you aim at remarkable things or only at your own thing—is so that it will be your life, your choice, your mistakes.”[9]

At the end of the day, we are all going to die. Sorry to be so morbid, but in 100 years from now, everyone that you know will most likely not be alive. This is just to say that you only get one life. It takes time and lots of trial and error to craft and curate the life that you really want. But this is perhaps the most important thing that any of us will be called to do. To be able to say that we lived the one life that we were given well. That we helped others. That we spent it doing something worthwhile. That is something that goes far beyond the praise, the achievements, the fancy titles, the salaries, and the approval of our status-driven institutions.

This endeavor takes courage. It takes deep reflection. It takes self-discovery. And it also takes learning a thing or two about your values. It is not too late. It is never too late. There are women in their 80s in my writing class who are just starting their memoirs, and it’s been amazing to hear their stories. Our stories matter. Our time matters. It’s up to us to dig deep, and figure out who we are, so that we can show up as our best selves in the world. So that we can create our best things. So that we can do our best work.

I’ll leave you with some parting words of wisdom from Cindy Gallop on the importance of discovering our values:

“Look into yourself, and identify who you are, what you stand for, what you believe in, what you value. Decide what your values are, and then operate accordingly to them. And when you do that, it makes life so much easier, because life will give you all the same shit it always will, but you’ll know exactly how to respond to it at any given situation in a way that is true to you. That way you are only ever operating for things that are true to you. And that is what matters, not what other people think.”

So, figure out who you are. Have the courage to keep trying, keep failing, keep testing and keep going. And live a life in accordance with your values that you can be proud of.

Many thanks to Alara Gebes for requesting this article, and to Deniz Kecik and Alan Jinich for their feedback.

If you enjoyed this article, please consider subscribing to the Misseducated Substack.

References

[1] Deresiewicz, W. (2014). Excellent sheep: The miseducation of the American elite and the way to a meaningful life.
[2] Ibid.
[3] Goldsmith, M., & Reiter, M. (2007). What got you here won't get you there: how successful people become even more successful. New York, NY, Hyperion.
[4] Gilbert, E., 2016. Big Magic: Bloomsbury Publishing.
[5]  Deresiewicz, W. (2014). Excellent sheep: The miseducation of the American elite and the way to a meaningful life.
[6] Ibid.
[7] Gilbert, E., 2016. Big Magic: Bloomsbury Publishing.
[8] Deresiewicz, W. (2014). Excellent sheep: The miseducation of the American elite and the way to a meaningful life.
[9] Ibid.
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