Mailbag: 25 year old "winner" on the default path: should I quit?

January 19th: Greetings! As you know, I’m on a mini sabbatical until March 1st. I wrote this post a couple of weeks ago.

If you haven’t filled out the reader survey, that would be a huge help:

(or survey here if you don’t have a Substack account)

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A reader sent me these questions and gave me permission to share them

Reader is a 25-years old who has always been a winner on her default path. Working on Wall Street but feeling deeply unfulfilled and thinking about exploring a career break.

#1 Have you ever regretted not stepping onto the pathless path earlier than you did? As someone who just turned 25 and only had 3.5 years of experience working full-time in a big global company, I wonder if this is too early for me to go on this path.

It’s so hard to actually consider rewinding the clock. I think I wish I had stayed at McKinsey longer. To me, it was a mistake to leave so quickly to go get an MBA when I was 25. That was pure prestige goggles, and the just a general restlessness to keep moving. It was such a great place to work, and I had a clear path with supportive managers to move into more challenging roles. I also had many good friends there. ‘

I got swept up in everyone around me applying for MBA and other grad programs. I think for me, a big part of this was just scarcity mindsey. I felt like I had snuck into McKinsey and wasn’t like the other people working there. I had an urgency to capitalize on my opportunities.

But by doing this, I ended up sort of adrift for the next 7 years, bouncing from one consulting firm to another. Also, that clear path for growth never happened again. I had an absurdly bad stretch of bad luck, ending up in three consecutive positions where the senior person in my department quit before I started.

In my final job, I worked with a partner who really challenged me and pushed me to work more independently and directly with clients. I gained a lot of confidence in that role, and it helped me feel like I could sell freelance projects on my own but that job had a lot of other issues, and I probably led to a lot of burnout and resentment that I spent years recovering from.

Despite these missteps, I was still learning a bunch of random things by moving jobs, shifting my focus over time, learning on my own, and doing stuff beyond work. Even though I certainly still learn and grow on my own, I do sometimes miss the structure of a workweek, deliverables, and good teammates pushing me to do better.

But the regret is less about staying so long and more that I stayed too long on a path with clearly declining motivation over time. Jumping from job to job helped increase short-run motivation and learning every time I leapt, but the trend was not in a good direction.

So the question is instead: Are you in the flow of tasks and activities where your energy and interest level are at least steady or growing? If not, what actions might you have to take to move closer to such a path?

It might be worth thinking less in years before you are “ready” than looking at the next job/gig/step as one that hopefully pushes you and challenges you in a way you are already wanting to get better. What are the jobs, places, or gigs you could pursue that would increase your odds of being on a path where you are progressing in the way you want to progress? I think there are many new kinds of jobs in this emergent hybrid economy between normal jobs and the creator economy that are really great places to work. Working for top creators, talent agencies, in social media, and startups can give you access to feedback on increasingly valuable skills.

I think stepping back, you likely need some story to make sense of it, and also some sense of what you are hoping to gain. I’ve called this “leap capital” recently, or the story you are telling yourself that helps you make sense of your transition. Is it a “one-year experiment” or is it a permanent leap? Big difference. And then, is this a way of testing out things you are already doing independently? Launching a creative experiment from scratch? Doubling down on something that’s working? Six months to goof off? It all depends. All can be fine for the right person.

Finally, other questions like:

• Financially, is it risky? If so, how could you derisk it?

• Emotionally, what might it cost you? Is that somehow potentially a way to grow in emotional capacity?

• What relationships will be worse because of it? Can you deal with that in the short term?

• Finally, is it reversible? Can you get back to where you are now?

Ultimately, I can’t tell you when it’s right for you. You need to decide what you are doing and why.

#2 Do you think you are lucky to have “succeeded” in the pathless path? Sometimes I see some comments online about taking a career break / quitting without the next job lined up, people talk about the risk of not being able to find a better job, and say it is not guaranteed everyone would thrive doing it.

You are projecting success onto me.

Others in my situation might feel like they are failing. Others might feel excellent.

Personally, I don’t really relate to the idea of “success” as much as you may not believe that.

One weird thing: I felt FAR better on this path almost immediately, and in the several years in which I was very much just breaking even without much intention to scale, grow, or make money.

Those positive feelings mostly came from the inner game of the pathless path - getting to know myself, my interests, my tradeoffs, my money insecurities, dancing and accepting fear and uncertainty and so on.

I spent the first few years of my path pushing the edges of this new kind of life and seeing what I might actually want to be doing. It was exciting. As soon as I started building my life around a creative practice, I found a life rhythm that felt good and sustainable and then the question was “how do I fund this?” I’ve been able to fund it for 8.5 years and I have some confidence I can keep it going for the next 2-3 years. After that? I’m not sure, but I’ll probably figure something out.

When I quit, I had nothing lined up. It was the first time I did that. It was scary, but it seemed like a better option than jumping from job to job like I did too many times in my twenties. Weirdly, it was not having a plan that enabled me to see how much running away from the present I was doing on my previous path. It forced me to see what I was actually doing, get to know myself, and start to figure out the tradeoffs that really matter.

Also, who cares about this:

“people talk about the risk of not being able to find a better job and say it is not guaranteed everyone would thrive doing it.”

So what. What do you think?

People have this weird tendency to make these broad claims like “well, everyone can’t do Y” to dismiss the possibility. It’s an uninteresting statement. So what? What if I say something like “Everyone can’t hit a tennis ball like Federer,” does that stop you from wanting to play tennis? No, of course not. Some things can be worth doing even if you don’t thrive. I certainly felt like I was fumbling around for the first couple of years there but never thought, damn, I should go back to my former path because I’ll feel less like a fool.

So what I am trying to tell you: I felt successful at the same time I felt like a fool. If there is a feeling I’d attach to success if you forced me, it would be contentment. Until I quit my job, I felt the opposite of that: restlessness.

For some people, they are totally fine with restlessness or just rank career success, steady incomes, money, and fitting in above that inner feeling of contentedness. I don’t, and I know that makes me weird. And poorer. That’s the thing: Every choice has a cost. What are you willing to pay?

We make a lot of tradeoffs that others would not be happy with. I only feel like I’m thriving because I am clear-sighted about the costs and benefits of the path for now and want to keep going.

Is that success? Who knows.

That’s for you to decide :-)

#3 Do you think you will ever go back to a full-time job anytime in the future? Do you think there could be a full-time job in the world that could be even better for you?

I don’t think I’d be open to 48 weeks of 5-day in-office employment. The good news is that there is a lot more dynamism in the labor economy now in terms of how companies are willing to work with people.

I think I could easily see myself in an ongoing part-time role for a company as an advisor, consultant, or something like that. I’ve built up a lot of skills that are probably useful to a lot of companies, but I’ve also learned how to structure different kinds of projects, gigs, and products in ways that don’t require in-person attendance to receive compensation. I don’t think money would make me want to work full-time again as long as I can hack together a modest living on a US salary.

But if our family changed our goals and decided it would be best for me to go pursue income to meet our needs, I would be the best positioned in the family to go earn money, so I’d do it.

But Angie is not pushing me to go to work and enjoys my flexibility as much as I do!

How important is it to have met your wife and have her company in your journey?

Very important.

We never really separated for more than a month after we met. She’s been with me from the early days, and we’ve been co-building this life together. I think my journey would have been a lot harder without her. In many moments of doubt, I felt normal because she was on a similar path.

I talk to a lot of people who say things like “how do you convince your partner to be on board with a different kind of life or path?”

I have no idea. I married a weirdo.

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Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

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• Kindred, a home-sharing app

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