Diversify Your Mental Portfolio
Two ways to gain further fulfillment--and protect a most precious asset
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
You can have enormous success in life and still be unfulfilled.
You can build tremendous personal wealth and still be unfulfilled.
Successful, wealthy people can struggle—like the rest of us—when they fill up on just one thing: Their careers.
This is a lesson from Devin Martin, an executive coach who helps hard-charging business leaders discover lifestyle integrity. I recently found his work through the Talking Billions podcast.
Several of Devin’s clients are investors. Ironically, these investors know the importance of diversifying their financial portfolios—but often fail to understand the importance of diversifying their mental portfolios.
Whether you’re working toward a billion-dollar exit or working for the weekend, a balanced portfolio of mental engagement pays off in your career and life. Here are two ways to get there…
Emotional Diversification
In his interview, Devin tells the story of a wealthy client in the “mid-nine figures” who was absolutely miserable. When asked about when he was last happy, the client told a story of 12 years ago, when he took the day off and watched movies all day…
“And the way he lit up telling the story, it broke my heart. It was such a beautiful memory, and it was so out of reach for him.”
Most of us are a long way from the nine-figure point, but we may feel a bit of this pain. In our leadership positions, we often take our work very personally. We’re waving the flag within the organization, encouraging our team to hit the next number, and navigating countless threats and opportunities—both real and imagined.
The win-loss balance of our workday defines the spirit we bring to the dinner table and into our children’s bedrooms at storytime. Or perhaps we put off the idea of marriage and family until the day when “work settles down”—thus postponing a key source of happiness.
You can get a long way with a complete focus on chasing down one thing. But even when you succeed by getting the promotion or selling your company, you can still feel unfulfilled. Expectations rise further, and stress along with it. Or you sell your company and find yourself kicked to the curb. The money is great, of course, but the meaning is lost. And it’s mostly the meaning that drives us to that success. I’ve been here twice.
And if you fail in your business venture, the depression that comes when you have put all of your ego eggs into this one basket is heavy. We feel that people look at us as losers. We wonder why our hard work didn’t pay off. I’ve been here, too.
It’s great to be emotional about our work and to take it personally. Still, we should diversify our emotional energy expenditure to balance our day and have something else to fall back on when our careers hit a bump.
Here are a couple of elements of an Emotional Diversification strategy that work for me:
Try everything—List all the hobbies and “someday stuff” that have piqued your interest over the years, and start giving them a go. Work with teachers and coaches who can provide the right baby steps. Tell your friends you’re up for anything and take them up on any offer to join them. As you expose yourself to these activities, consider whether and how they grab you.
Go deep on what you love—Once you find something that trips your trigger, invest real time into it for the long haul. Here, you’ll often have to overcome the bumps and bruises of skill building. Most hobbies are not rewarding until you’ve put in many hours. But, like compounding interest, the more you work, the better you get and the more fun it is. For me, playing guitar has been an incredible journey. I took my first lesson seven years ago, at age 45. Through the years, I’ve gone from blistered fingers on basic chords to barre chords, singing, playing in a band, and now recording my own music. You can also do “fully engaged sprints.” For example, plan a trip to France but spend six months learning French and reading books on French history beforehand.
Get it on the schedule—The key is to commit, which means building a habit and blocking out time for these activities. I play guitar most nights right after cleaning up the kitchen after dinner. I read a book with my coffee every morning for an hour. I exercise after the work day is done. Put your phone on Do Not Disturb during these sessions. Blocking your schedule and building the habit helps you start a practice and validate that it is critical for your mental, physical, and emotional health.
And for a BONUS, try to take on a new interest with your significant other. My wife started playing tennis last summer, and I jumped at the chance to hit balls with her. I had not picked up a racquet since college. Tennis isn’t my favorite sport, but the opportunity for us to spend quality time together makes it so much sweeter. She’s taking her first golf lesson today, and I’m eager to hit the links with her soon. Who knows what we’ll do next?
Social Diversification
I discovered Devin’s podcast through a newly formed group called Leading Edge. I had been following the reading and speaking of its founder, Tom Morgan. When he offered me the chance to join, I leaped at it. The group comprises people who desire to investigate new paths to meaning in work and life. I joined in part because I’m always looking for Social Diversification.
Humans are highly social creatures. We work together to do almost everything. Much of our fears come from being cast outside of a social group. Our personalities are shaped by the people closest to us.
We can get very close to our co-workers. We spend more time with them than some of our dearest friends and family members—and we’re brought even closer by teaming up to overcome challenges and achieve great things. There can be a fine line between a great company culture and a religious cult. Both can demand a complete investment. But we’ve got to diversify our social groups, too.
The book Collective Illusions describes social concentration's dangers and warns of an “Identity Trap” when our thinking gets too narrow, and we put up walls to outsiders. And we feel pain when we get kicked out of the circle of our work friend group. Each corporate layoff rips people out of social bonds that add meaning to work and life.
But by diversifying our social circles, we are more able to handle the ups and downs at the office. Meeting other people also gives us a broader support network and more insights into how the world works. Ironically, this makes us even better in our careers:
“Identity complexity is also good for our groups. Just as we need to build up our immune systems by exposing ourselves to various germs, our groups can only survive and thrive by adapting to change.”—Collective Illusions
If you’re ready to broaden your groups, here are some suggestions that might help:
Don’t be shy—As Collective Illusions suggests: “It doesn’t really matter what affinity groups you choose to join. They just need to hold some positive, personal significance to you. You can join a sports or music fan group; a book club, game night, or study group; a garage band or a choir; or just about anything else that engages you and is sure to make you feel happy on a regular basis.”
Commit to meeting—Once again, get it on the calendar, or you won’t make the time. I’ve got a group of friends from the agency we last worked at 15 years ago. Each year, we take at least one long weekend trip together. It takes time and planning, but consistently seeing this group is incredibly energizing.
Combine with your other passions—Kill two birds with one stone by diving into a new hobby with a social element. There are in-person and online groups for every hobby you may take up. The social group will also add peer pressure to keep you working on your interests.
Meet the neighbors—In New York City, during business school, my wife and I had a tiny apartment in the West Village. I loved it there, but I have one big regret: I never met anyone in our building for over two years. Since then, I’ve gotten better. We moved to downtown Cincinnati a few years ago, and I’ve made incredible friendships with our neighbors. We have a weekly trivia team, a monthly happy hour, and a Slack channel. Life is so much better when we dare to step out and bond with the people we live near.
You never know how your interactions with others can improve your lives. I recently had a one-on-one chat with a fellow Leading Edge member. I’m a bit farther down the road on my startup travels and was able to bring some perspective that he hasn’t gotten from the Silicon Valley bubble. At the end of our chat, he thanked me for “defragging his hard drive.” That made my day.
The Ultimate Exit
While building my last startup, I thought little of what I would do once we were acquired. It always felt a long way off, and I had too much fun building it up with our fantastic team. After the sale, we got to celebrate together. Then I was out on my ass—wandering in the woods and wondering what to do next.
The other day, I found a paper by Yale professors called “What’s Next: The Entrepreneur’s Epilogue and the Paradox of Success.” It describes how post-exit entrepreneurs typically struggle and how they can best move forward. It’s nice to see this is a common issue for entrepreneurs. I just wish I had access to this four years ago!
Fortunately, with time and by diversifying my interests and connections, I think I’m on the right track for the rest of my career. My play now lies in finding ways to scale what I’ve learned about building high-performance organizations. Writing here has become a big part of this. I love that I can reach thousands of people each week. And it’s why we launched Fleet, our holding company that backs service business leaders. We hope to have thousands of employees in the years ahead.
But I also invest a good amount of my time into life improvement. I’m reading and discussing history, philosophy, religion, and more. I’ve gotten into yoga, meditation, breathwork, and other mind-opening experiences. Figuring out what’s happening in my mind and building better habits has been fascinating.
I’m finding it a journey that makes each day more precious and improves my work performance and personal relationships. Ultimately, it’s a part of going as far as I can in this life before the ultimate “exit event.” Let’s hope that’s a ways off…
How we might work together…
Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
Looking for Influencer Marketing and Content Creation? The team from our previous company is back by popular demand with A2 Influence. We’re ramping up now and would love to share more.
Feel free to schedule a time during my Office Hours to discuss questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Neal Stephenson’s creative process
First, THE Neal Stephenson—is on Substack! (@Brad Berens OMG!!!) He’s the author of several excellent world-building fiction books covering topics from medieval sword duels to cyberspace.
I’m digging the posts on his creative process and work outside of writing—especially this one, creatively titled Cow Milking, Cud Chewing, and Flying Monkeys. His main point, very relevant to my post above, is:
“You can’t milk a cow 24/7. You have to milk her for a short time and then let her go out to pasture and be a cow for the rest of the day, chewing her cud and so on. Likewise with writing or any other form of focused creative work.”
After a few hours of this first-in-the-morning creative process, Stephenson moves on to other interests. These other interests keep him engaged and learning while allowing his current creative project process to process in the background. Whatever his secret is, a lot of us love the output.
You’ll have to read the post to find out what Flying Monkey’s are. I guarantee you’ve got a few sitting in your inbox…