Five steps to recreate your career (Part 2)

Four years ago I embarked on an abrupt career transformation. I went from hedge fund researcher to creative solopreneur (with a messy discovery process in the middle). I recently launched a new podcast with Quartz called FWD: Thinking (iTunes, Spotify) and interviewed five bold professionals who have challenged the status quo in the pursuit of meaningful work. Here’s a two-part series on how anyone can jumpstart their own careers, without quitting their jobs. And don’t miss the series on Instagram.


  • Stop looking for meaning
  • Resisting labels creates opportunity
  • There are lots of ways to make money
  • Develop your inner game
  • Question what freedom means to you


Stop looking for meaning

“Good work, done well for the right reasons.” Jerry Colonna (aka the man who makes founders cry) has coached countless executives and succinctly summarizes how our careers satisfy a core human need. But what are the right reasons? Let’s say you’re “enlightened” about your career and are able to look past the trappings of wealth and status as an underlying motivator. That’s probably not enough. We want to know that the work we’re doing matters; the proverbial hunt for meaning.

The default definition of meaning is Hollywood-esque: alleviating poverty, combatting climate change, running for office. And more than ever, the world needs talented people to take on these BHAGs. But please – I beg you – don’t fall into the trap of believing that these are the only ways to make your work meaningful.

So what happens if you’re a Vice President at a finance firm or on the partner track at a law firm? Where’s the meaning of working furiously on an M&A deal or an internal presentation that will never see the light of day? On the FWD: Thinking Podcast, Brad Katsuyama, the founder of IEX (and main character from Michael Lewis’ book Flash Boys) told me:

“I think there’s meaning you can find in a lot of work. I hate putting spotlights on just totally extraordinary missions because there’s mission to be found in a lot of places.”

Meaning can be found in how you mentor your team, the ways in which you show up as a partner and parent, and how you treat others. If you’re looking for more, it can be found through volunteering, side projects, and involvement in your community.

Even if you’re not quitting: Widen your own aperture around meaningful work. Take a mental inventory of where you have a personal impact on someone else’s life. And think about the bigger causes you care about. How can you commit a small portion of your time to pushing them forward?

Resisting labels creates opportunity

There’s a common cocktail party question that makes my stomach turn and my skin crawl: What do you do? I abhor this question and it was the bane of my existence during the early days of my career reinvention. It triggered insecurities that almost sent me back into the workforce. Why is this question to debilitating?

It begins with how much we intertwine career with identity. We say “I’m a doctor” or “I’m a hedge fund manager” as opposed to “I work in medicine” or “I make investments.” Next, we’re intellectually lazy. Labels help us craft narratives about ourselves, that in turn, situates us within our peer group. And our natural instincts are always to know where we stand relative to our tribe.

But labels are fabricated social constructs and extremely restrictive. Every single one of you is a beautiful mix of intellect, talent, personality, and passion. There’s no damn label for that (other than Tribe of One). And the more you move away from a traditional career track, the harder it will be to ascribe a label to it. And that may feel like a bad thing, but ultimately it opens up possibility.

These days, I spend 2-3 hours a day writing. My impostor syndrome makes it hard for me to identify as a writer, after all, I was a computer science major who’s never taken a single writing class. But as you can see below, the activity of writing, has opened up an endless possibility of activities that are both fun and monetizable skills.

Even if you’re not quitting: Play a game with yourself in social situations. Avoiding ever asking people what they do. Try to learn as much about them and their motivations without directly talking about work as a professional identity. I guarantee you’ll be surprised by what you’ll uncover.

There are lots of ways to make money

This is a natural segue to the section about expanding possibility by resisting labels. A core personal thesis is that careers are being unbundled due to the commodification of the technology stack. This is enabling the growth of non-VC funded businesses but also what longtime RadReader Tiago Forte calls the full stack free-lancer:

They leverage software-as-a-service and online platforms to vertically integrate a “full stack” of capabilities, instead of focusing on one narrow function. This allows them to capture a much greater percentage of the value they create, instead of giving it away to gatekeepers and distribution bottlenecks. Full-Stack Freelancers are responding to a series of technology-driven trends — contingent employment, intensifying globalization, and automation — by taking advantage of the other side of the coin: technology finally becoming powerful enough, cheap enough, and user-friendly enough to be deployed productively by a single individual.

It really hit me when I was able to paste one line of code onto my website to start accepting credit card payments. When your business infrastructure is so easy and cheap to set up, it frees up time for the more challenging parts: creativity and finding customers. My own trojan horse has been writing, which has truly enabled me to create my own luck. And my sources of revenue continue to shape-shift as I hone my skills, while experimenting with what works best:

Even if you’re not quitting: Big corporations do not understand the power of the stack. Learn how to use a handful of these apps and services to creatively solve new problems in your workplace. Try Airtable as a new take on spreadsheets or to create a beautiful responsive site showcasing your talents.

Develop your inner game

Talent is overrated. I was a B student at Yale and I think that I’m very much right of center in a normal distribution. Above average, but not uniquely talented (yet I can punch above my weight by logging the hours). And I’ve seen many entrepreneurs leave the corporate world only to flame out and return in less than a year.

Why is that? They fail at the inner game. The outer game is coding, writing, building, hiring, and operating. And while these are hard, IMHO they represent table stakes. The inner game involves defying labels (mentioned earlier) emotional self-regulation and shifting out of a scarcity mindset.

Keynes wrote “The market can remain irrational longer than you can remain liquid.” I adopted this for entrepreneurship as follows:

The outside world’s perception of you can remain irrational longer than you can remain emotionally solvent.

Rarely a day goes by when something “goes wrong” as an entrepreneur. And in the early days, a passive comment from a friend or peer could easily send me into a whirlwind of self doubt. An entire book could be written on this topic (ahem, but here are a few takeaways: avoiding fear as a self-motivator, not viewing feedback as a threat to identity, and defining success on your own terms. Shifting out of a scarcity mindset entails truly believing that you have enough time, money, opportunity, and love. Internalizing that we don’t have enough leads us to believe that we are not enough.

Even if you’re not quitting: Talk about your insecurities with someone who cares about you, but is not emotionally invested in you like a therapist or a coach.

Question what freedom means to you

At the end of the day, reinvention is ultimately about freedom. The freedom to pick your boss or co-workers, travel, work remotely, ditch the 9-to-5. For me, one of the best parts of being an entrepreneur is that it provides the flexibility to spend a lot of time with my young kids. Yet, I probably still work 60 hours a week (including five hours, every single Saturday for the past 192 weeks). Am I really free? Let’s deconstruct what freedom might mean:


  • Financial freedom
  • Freedom from authority
  • Freedom from a schedule
  • Freedom of choice
  • Geographic freedom


Seems reasonable, right? But when you probe on these freedoms it turns out the answers aren’t as straightforward as you’d think:


  • Financial freedom – Many people can’t answer the question “If you won the lottery, how would you spend the next five years of your life?”
  • Freedom from authority – Many people want to be told what to do and cannot self-motivate or learn in a self-directed manner.
  • Freedom from a schedule – Many people crave structure in their days.
  • Freedom of choice – Too much choice can be overwhelming (see the Paradox of Choice).
  • Geographic freedom – Travel rarely cures an unsettled mind and most people want to “nest” and build a home.


But there’s more. And here’s where the emotional self-regulation kicks in. What about freedom that originates from within?


  • Freedom from others’ expectations
  • Freedom from the relentless pursuit of excellence
  • Freedom from your most negative thoughts


So even if you’re not quitting, every single one of us should contemplate and consider: What does freedom mean to me? If might significantly change the path of your own career reinvention story.

Thank you for plowing through this series. I’ve started a coaching practice to help others work through scarcity thinking and their relationship with money. Hit me at khe [at] radreads [dot] co to learn more.

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