5 Tough Choices You’ll Face When You Reinvent Yourself
Reunited with my best friends from McGill University in August, 2014. This was the moment I realized I had to leave Wall Street and rebuild my life. From left to right: Alex Fane, Mauricio Delfin, Bradley Chisholm, Mike Falsetto, and me.
There are moments in life which shock you into a sudden sense of urgency to get your $h*t together.
Marriage, birth, divorce, death, illness, and DWIs are a few of the more common shocks. One of my big ones happened at a reunion with my best friends from college at a lake house outside of Montreal in August of 2014, 14 years after we graduated.
Through a series of acquisitions, accidents, and miscalculations I had become a miserable, disenchanted, upper-middle manager on Wall Street. On paper I was director of innovation at Bloomberg. In real life I was a disgruntled political operative. I hadn’t built anything that mattered in years. I was stuck, scared, and despondent.
I knew I had to leave. Except there was a problem: I was a grownup now. I had two kids, a mortgage, and a phenomenal wife who depended on my benefits and salary. Why couldn’t I just suck it up like every other schmuck who collects a salary and hates their job?
There was huge tension between my immediate financial responsibilities and my obligation to build a life that I loved.
That was 9 years ago this August. Within a year from that reunion I had left Bloomberg, was consulting for Google and PWC, and had begun writing my first book “This Might Get Me Fired.” Leaving and starting over was the scariest and most rewarding decision I ever made in my adult life.
I think a lot of people experience what I went through that August toward the end of summer vacation. They’ve had a few weeks to ask themselves, “how am I doing?” And sometimes the answer that comes back is “not good. Get your $h*t together.”
I don’t want to turn this into some self-help article about how to reinvent your life after you leave a huge company. (and anyone who claims to have a recipe for that is lying to you). I want to be completely honest about some of the tough choices I had to navigate and share what worked for me.
Tough Choice 1. Pursue happiness or pay your mortgage. Pick one.
This was a false choice that felt real at the time. I knew that I wouldn’t be able to last at a job that I didn’t like. I had a clear hierarchy of needs that I knew I needed to honor:
1. Find my tribe
2. Make an impact
3. Make money
Making money was just as important as finding my people and making an impact. But it was dependent on those first two conditions being met. Once I understood that about myself it was easier for me to pursue what was right for me, and say no to everything else.
Tough Choice 2: Startup, consulting, or another corporate job?
It took me about 2 weeks to realize that I couldn’t go back to my startup roots. I wasn’t 25 anymore. The economic volatility of a startup wasn’t compatible with my adult financial responsibilities. I also met too many 23 year olds who fully subscribed to hustle culture and listened to bad EDM, and I was frankly too old for that $hit (even though I wasn’t yet 40).
I soon landed a consulting engagement with Viacom, and soon another engagement with PWC and Google. And they paid more than I was making on Wall Street.
I quickly realized that I was immediately differentiated from every other consultant. I was a survivor in a field of observers. Very few consultants had experienced the obstructionism and politics that keeps essential change and innovation from happening in big companies. They thought innovation was the blockchain and agile. I knew exactly what my clients were going through. And I had a battle-hardened understanding of how to get through it. My hard-earned empathy was my biggest unfair competitive advantage. Your scars are your superpower. Remember that.
Eventually I pivoted my consulting practice into a startup, Punks & Pinstripes. Which is a vetted community for entrepreneurs who leave big companies to launch new ventures.
Tough Choice 3: Invest in a coach or a community?
The stupidest mistake I made when I left Bloomberg was spending $2000 to become a certified SCRUM product owner. I had already launched 22 products in 5 different companies by then. As if I needed some badge to prove it.
After that I made my second stupidest mistake and hired a $20,000 executive coach who’d never been an executive.
What I needed was the support and solidarity of people who had been where I was. I needed to know how they stayed resilient when they were scared, or filled with self doubt. I needed to know how they got unstuck when they were wrestling with the problems I wrestled with. All my biggest client introductions, friends, and trusted colleagues materialized because someone who had a pure interest in me being ok introduced me to them. This is why so many of my clients are still part of my life, and will be for a long time.
So, find a community of your peers and invest in it. (Yes, I’m biased here. I run a vetted community for entrepreneurs who left corporate leadership to launch new ventures, Punks & Pinstripes. Being biased doesn’t make me wrong.)
Tough Choice 4. Invest in relationships or branding?
A third stupid investment I made when I was just starting out was hiring a creative director to design my website, logo, and business cards. (It was called Bowery 315, the address of the mecca of punk music, CBGB’s, FYI).
I mistakenly believed I needed to be like Gary Vaynerchuck to find clients. The truth was I needed to answer three questions:
What is the biggest pain point of my ideal customer?
What can I offer them that no one else can?
How can I demonstrate my value to them?
When you embark on a new venture you are bombarded by constant pressure to buy paid ads, hire a social media consultant, a PR consultant, and to go viral. Unless you’re selling a retail product, that’s total bullshit. You’re better served going for coffee with someone who inspires you, who you admire, and who you trust. If they feel the same way about you they’ll become a customer.
Tough Choice 5: Should I freak out or stay calm?
One of my signature strengths is beating the shit out of myself for things that I can’t control.
One of the hardest adjustments for me to make when I left a huge corporation was how much was out of my control. I couldn’t control when I’d find a lead, close a sale, whether an article would get picked up, whether a client was happy, whether a client would pay my past-due invoice. I did have greater control over who I worked with, what I worked on, how I expressed myself.
At a certain point I had to actively choose to not beat myself up about the things I couldn’t control. (I also had to learn from my mistakes and get better at selling, closing, and managing cashflow). It was my job to honor my hierarchy of needs: 1. Serve my tribe, 2. Make an impact, and 3. Make money. The most important investment I have learned to make is to feel fulfilled by my work even when the outcomes that are out of my control don’t go my way. I have no idea how that happened. But It did and I’m grateful.
Y’all are my heroes,
Greg Larkin
Founder, CEO, Punks & Pinstripes
If you like this article, please:
Subscribe and share it.
The next opportunity to become a member of Punks & Pinstripes is Sept. 8 - 22. We only accept 25 new members during a 2-week application period every quarter, and membership is capped at 200.
