The Five Best Decisions I Ever Made

Chip Conley calls those of us in midlife (ahem) who can think holistically and harness the emotional intelligence that comes with years of human experience “modern elders.” And I’m OK with this title because, like Conley, I believe more intergenerational learning can enhance and evolve our companies, networks, and communities. 

So in the spirit of knowledge sharing, I started reflecting on some of the most formative moments in my life. Listing below (in chronological order) the five best decisions I’ve ever made, hoping that something resonates -- whether you're just starting out or a fellow traveler on the modern elder highway…

Starting my business – When I quit my job in a well-paying corporate training program to start my own company in my twenties, “entrepreneur” might as well have been a funny French word for unemployed. There was no hustle culture, no sitcoms spoofing Silicon Valley, and no venture funds handing out seven-figure investments to new founders. There was just me, the $800 in my bank account, and the business cards my dad was kind enough to have his advertising director print up for me. If I didn’t generate sales, I couldn’t pay my rent; and while the story ends well, there were countless sleepless nights across multiple companies where I worried it would not. 

Deciding to leave corporate America was a big step, but it gave me the ultimate freedom: to determine the pace and trajectory of my life. It’s not easy being your own boss - and it’s certainly not for everyone - but the freedom and flexibility it afforded me professionally was a revelation. It’s also evolved into an entire way of thinking about my personal life. Freedom underpins so many of my choices as a result…choices about the kind of individual I want to be,  the kind of impact I want to have, how my family and I move through the world, and more.

Choosing the right partner – Who you spend your days with is as important as how you spend them. And I’m glad every day that I chose my wife. I often say that just because you’re in love doesn’t mean you should get married, and I offer this up because if my wife and I didn’t share more than just love, I’m not sure how the last two-plus decades would have unfolded. Life is like a giant stress test for marriage. Personal, professional, or both challenges are inevitable, and they will come for you fast and furious. They certainly did for us. And I don't want to preach because we should all be able to decide exactly what our chosen family looks like. So I’ll say this: I believe that sharing values with your partner, talking about whom you aspire to be, and being aligned about how you want to move through the world as individuals, as a couple, or even as a family (if you decide to go that route) is the best preparation for the inevitable surprises, disappointments, and more that life will send your way…

Joining Entrepreneurs Organization (EO) – Self-help guru Jim Rohn famously said, “You are the average of the five people you spend the most time with.” It will shock no one who has ever been (or had!) a teenager that this is useful advice to learn sooner rather than later. But it resonates most for me with the peers I met in my thirties and forties through EO, an organization that has led to some of my deepest and most profound friendships. Perhaps it dates back to my first decision to strike out on my own, but surrounding myself with people I admire and who challenge and inspire me daily has profoundly impacted my growth and development. So I think it’s critical to seek out friends who lift you up, push you to be your best self, and help you grow…

Moving to Spain – Leaping to live and work remotely seems almost quaint in the age of WFH, WFA, or whatever we call this latest phase of hybrid work. But packing up and moving abroad ten years ago with my wife and three elementary school-age children was a big risk back then. It was a brash experiment in getting outside our comfort zone that, luckily, yielded some of the best moments in my adult life. So if you have the opportunity (or the luxury) of working from anywhere, I highly recommend going for it – a radical change in your environment can be transformative. Our years as ex-pats continue to pay dividends to my entire family in wonderful and unexpected ways. We immortalized everything we learned in a single graphic, so check out our Barcelona Manifesto if you need inspiration. 

Selling my business – In the spirit of coming full circle, it seems only appropriate to close out this list with the decision to sell my last business a few years back. Not only did that provide me with a path to my current gig working with Teamshares, where I support former owners with their transitions, but also it taught me that letting go is never easy. Seth Godin talks about the three curves in life in his book The Dip, and with one of my businesses in particular, it was hard to know for a while there just which curve I was in: Was it a dip I would come out of? Was I trapped in a cul de sac, where I would keep circling around exponential growth but never quite get there? Or was I about to go over a theoretical cliff I could never have seen coming? My industry was changing, and I was resistant after fifteen years to invest even more capital to keep pace with the evolving marketplace. But what if I missed a downturn or was unprepared for a seismic shift that caught me off guard? 

Timing is everything when selling a business. I was fortunate to get that and other salient advice (see decision #3) as I wrestled with cashing out versus pressing on with a profitable business that afforded me countless freedoms (see decision #1). It was only after I sold that particular company that I realized how critical a well-planned transition is – no matter where you are in the lifecycle of your business. You may love owning and running your company (or companies) today. But at some point, whether it’s age or circumstance or both, you will want to step back, and acknowledging and planning for that inevitability is crucial to a good exit, as is understanding both the financial and emotional impact of a life-changing decision like selling your company.

I’m thinking a lot these days about how to share my experience and help others navigate what to look for in a transaction, as well as how to process a transition and come out better on the other side.

I’ve been so blessed with mentors and friends -- let's call them my personal modern elders -- who’ve shared knowledge and provided signposts for me along my business and personal journey. Sharing some of my decisions and lessons learned is how I can pay it forward for those of you who find yourselves at a professional or personal crossroads. Have a life-changing decision you want to share some wisdom about? Drop it in the comments so we can all keep learning together.