Five steps to recreate your career (Part 1)

My new podcast FWD: Thinking (iTunes, Spotify) is about recreating your career. This season, I’ll interview bold professionals who have challenged the status quo in the pursuit of meaningful work. In each episode, I also reflect upon my own reinvention from Wall Street analyst to creative solopreneur. Here are five steps that anyone can apply to jumpstart their own reinvention (and stay tuned for part II next week). And check out this post on Instagram.


  • Be in service to others
  • Find your tribe (they’re out there)
  • Financial decisions you made in your 20s matter (and are reversible)
  • Favor streams over containers
  • Stop reading, start doing


Be in service to others

When I reflect back on my Wall Street skills a few jump out: I relished technical details, I could ferret out new opportunities quickly and was a workhorse in logging the hours to get sh*t done. These traits have all served me well as an entrepreneur, but I realize now that they’re just table stakes. My (not-so-secret) secret weapon was that I loved being in service to others: as a boss, a “networker”, and as a friend.

At first, when I started the RadReads email newsletter this wasn’t obvious. But I realized that the curation of articles was not only something I was good at, but I enjoyed providing it as a “service” to others. This philosophy extends into social media, talks, articles, and podcasts. My mission first and foremost is to be in service to you, the RadReads community.

Even if you’re not quitting: How can you add value to other people’s lives? Does technology enable you to widen that reach?

Find your tribe (they’re out there)

When I quit, I thought that I’d be the only person crazy enough to leave a high paying job and attempt to strike out on my own. And boy was I surprised to find out that the world is flush with corporate misfits and rebels, each blazing their own unique trails. The loss of identity in leaving a corporate job can be jarring and combined with the uncertainty of entrepreneurship, it’s easy to feel lost and lonely.

But then you realize that there are people who have been doing it for years (and in some instances decades) as well as others who are plotting their exits. There’s an unspoken code amongst entrepreneurs, a tacit understanding of the courage it takes to leave something known. And as a result, competition melts away – people go out of their ways to help you, talk you down, and help you avoid the mistakes they’ve made.

Here’s where tech comes in; “engagement” gets a bad rap. It’s the dopamine-inducing games that the the social media giants play to get us addicted to their platforms. But it also means engaging with someone whom you respect, find interesting, or can be in service to. And bringing authenticity and generosity to social media is a key way to identify and build that tribe.

Even if you’re not quitting: Find your digital tribe. If you’re not comfortable with social media, treat it like a cocktail party. Look around. Observe cues. See who’s more welcoming. Be kind. Regardless of your age or industry, this will add richness to your life. (Listen to the Gen Z whisperer’s advice on this.)

Decisions you made in your 20s matter (and are reversible)

The FIRE (or Financial Independence, Retire Early) movement is in vogue with millennials these days; I’m thankful that I stumbled into its principles as a college kid in 1997. It’s actually not that complicated: save a lot, invest early, minimize taxes and fees. But there were two distinct behaviors from my 20s that have given me a huge financial buffer as an entrepreneur.

First, I never got caught up in the lifestyle creep game. Thankfully, I never cared for the explicit trappings of luxury: cars, watches, vacation homes, and wine collecting. There were years when my income doubled (in fact, it once quintupled) but my spending would increase by 5-15%.  The difference went directly into the stock market. No questions asked. No market timing. Just one lump sum.

Second, when it comes to investing, I get out of my own way. I actually don’t enjoy investing, I view it more like eating broccoli. Both support the things in life that bring me joy: being with family, creating Rad stuff, and being active and outdoors. I don’t trade, in fact, I’ve never sold a share of the SP 500 index since I was 17 years old. And whenever I’m tempted to make an investment decision, I remind myself of a Fidelity study which showed that the best performing accounts were the ones that forgot they had an account!

Even if you’re not in quitting (or in your 20s): You have agency over your spending. Repeat after me. You have agency over your spending. Houses can be sold; leases can be bought out; private school is not the only option; and believe it or not, children can’t tell the difference between a motel pool and a Four Seasons pool. And even if you don’t want to quit, being intentional about your savings is a surefire path to freedom.

Favor streams over containers

I get a kick out of watching my fellow Gen X’ers move from a Microsoft Office to a Google Docs work environment. Many of them are aghast at the fact that you can’t “seal off” a document from endless revisions. (Some have even resorted to printing them out as PDFs to crystallize its contents!) This is the perfect metaphor for a world that is moving from containers to streams. A few examples:


  • Email → Slack
  • Static web → Feeds
  • Albums → Streaming
  • Books → Blogs (note: I realize this is way more nuanced, but roll with me)


The implications are that the world is no longer waiting for your perfectly crafted product or project (i.e. container). It wants to see the living document grow, then self-edit, than transform into something better (i.e. stream). This means that the Pareto Principle (better known as the 80/20 rule) kicks into overdrive and that it’s ok for projects to be raw, messy, unfinished and WIPs. And that’s the easy part. The harder part is letting go of perfectionist tendencies and welcoming feedback (and critiques) to make your final project better.

Even if you’re not quitting: Take an existing project and tinker endlessly. Favor fast (and sloppy) iteration over perfection. Ensure that you have very tight feedback loops and that you actually take the feedback into consideration.

Stop reading, start doing

Just start. The abundance of information out there can make it tempting to read about the actual thing you want to do next, be it coding, blogging, creating music, or starting a business. Look deep inside: what’s preventing you from starting your project? Fear of failing? Lack of confidence? Complacency around your existing situation? Confusion about what sets of actions to take? In a brief but incisive post (which inspired this paragraph) Can Duruk writes:

It really is another form of procrastination, if not a more dangerous one in my opinion, than randomly starting to play a video game. The fact that you can fool yourself, for the most part, into thinking that you have done something really valuable with your time is really dangerous. 

Even if you’re not quitting: What activity in your life are you avoiding? Take a look at where you’re spending money, watching YouTube videos, or talking the talk – without walking the walk. Investigate the deeper root cause behind the inaction.

Next week in Part II, I’ll cover:

  1. Don’t look for meaning
  2. Resisting labels creates opportunities
  3. There’s lots of ways to make money
  4. The inside game is way harder
  5. Freedom is overrated

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