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Every two weeks, I share my writing about investing, career transitions, parenting, and other topics that engage me. I'm just trying to figure stuff out.

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Evolving Advice on Career Pivots

Welcome to the first of a two-part post. The first part outlines the foundational advice I've shared with those seeking advice for mid-career pivots, plus one of two points I've added recently. In part two, I'll explain why I've recently been recommending a simple personal finance book and how the ideas in this book have profoundly altered my thinking about work and life.

First, a brief recap. In December 2021, I left the world of finance and launched a career pivot with no clear destination in mind.

I expected the search process to take a year or more, so I prepared for a long grind. But I was lucky. Within four months, I landed a meaningful role as COO at Circa, where we're working to solve an important problem in a massive market.

When viewed through the lens of LinkedIn, it looks like I cracked the code. As a result, mid-career professionals, usually in finance, regularly contact me for advice on executing the pivot. I always welcome these conversations since others generously did the same for me. Remember to pay it forward! While I have some valuable insights, there's no simple, all-encompassing answer.

Two Pillars: Create Luck and Build a Framework

Typically, I start these conversations by sharing two strategies that helped me immensely: create luck and build a framework.

Luck helped a lot, at least in terms of timing. Certainly, I helped to improve my odds of success by activating my generous network, but fortune will always play a role. At a minimum, good luck will accelerate the process. Two months ago, I wrote about this topic on LinkedIn. You can read that post here if you want more. For now, I'll keep things moving.

The second pillar, building a framework, helps when you need help figuring out where to start.

Rather than limiting myself to the default off-ramps for finance folks in their fifties, I wanted to uncover a wider opportunity set. So I kept an open mind rather than targeting a specific role or company. My coach Kathy Vines and I created a simple framework - the "BIG IF" - to guide the exploration process.

• B - Belonging - must feel a personal connection with the team
• I - Impact - my role matters, and the company is doing something meaningful
• G - Growth - personal growth and also a business that is growing
• I - Income - enough, not just more
• F - Flexibility - an entrepreneurial culture focused on output and contribution, not face time

The exercise itself will help clarify what's most important. What are the non-negotiables in your next role? What do you need? What have you enjoyed most about your work experience? In what types of environments do you thrive?

Armed with the BIG IF as a screening tool, I had many interesting conversations about roles I'd never have considered otherwise. If an opportunity met this minimum standard, I investigated it.

When I began searching, I wrote on LinkedIn, "There's a good chance that a year from now, what I'm doing is something I've never even thought of."

The guess was 100% correct.

I couldn't see then what's obvious now; a senior role at a proptech startup perfectly married my experience in multifamily, skills, and a desire for more impact and meaning. Plus, I got to develop my geeky fascination with leveraging technology to improve processes.

The key point is that proptech startup was not on my initial list. A framework empowered me to wander down new and unexpected paths.

Be prepared: you'll probably find leaping into the unknown both uncomfortable and uncertain. But it might be just what you need. It was for me.

What else?

In more recent career change conversations, I've added two more nuggets.

The first bit of advice is familiar. It's not completely new - just a stronger emphasis on the "B," for belonging, in "BIG IF."

Work requires substantial time and energy. That's true whether you're thriving in a meaningful role or punching the clock. Of course, the work itself matters. But as I've thought more about it, the people around you influence the quality of that experience at least as much as the work itself.

In modern society, work serves many roles in addition to providing income. We discover meaningful connections through our work. Colleagues become close friends. I even met my wife at work.

Humans crave a sense of purpose and want to feel connected to others. Work ticks that box for many people. Whether work should carry such a heavy burden is a better question but also beyond the scope of this post.

Like it or not, we spend much of our waking hours and energy on work with teammates and colleagues. That's time and energy we cannot dedicate to friends, family, and other activities.

Think carefully about how you will interact with these people. How do they manage inevitable disagreements? Are you energized when you spend time with your colleagues? Do they care about you? Will they challenge you constructively, or will they tear you down?

Many of us remember the people we've met on our journey more than the tasks and projects we completed.

Conclusion

When people ask for my advice on what worked in my career pivot, I've relied on two fundamental suggestions: create luck and build a framework. More recently, I've stressed the importance of connecting positively with your potential colleagues.

In two weeks, I'll tell you how an unlikely book has dramatically shifted my mindset around personal finance. And because personal finance fears, real or perceived, often affect our career choices, I now recommend anyone considering a career change read this book. It can massively unlock your opportunities in powerful and unexpected ways.

Happy 4th!

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Other Stuff

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​Read the article (18 mins)

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​Listen to the podcast (1 hr)

“For Grief” by John O’Donohue In early June, I lost my mother-in-law to cancer. And then later in the month, a good friend passed away in his sleep of unknown causes at the age of 51. I wanted to share this poem by the late Irish poet John O'Donohue with those also navigating the grieving process. O'Donohue had a gift for helping others make sense of the human experience with his words. He gently reminds us that we will eventually find peace with the loss of our loved ones. For those readers carrying the heavy weight of grief, I hope this poem helps a bit.

​Read the full poem (as long as it takes)

And a Farewell Photo...