Riches that Rival Bezos, Buffett and Bailey

Regrets. It’s a common theme with many articles written about everything from regretting time not spent with family and friends, to not following one’s heart to sticking it out in jobs they hate. This piece, however, is not a declaration of regrets. Mainly because I don’t have any. I’m truly blessed with my family, friends and career.

That said, every life deserves introspection. It’s an opportunity to reflect on your blessings and, perhaps, adjust your course to build on such good fortune. And if you’re just starting out, maybe I can give you the benefit of my experience.

If you’ve seen Frank Capra’s movie It’s a Wonderful Life, you know the story of George Bailey who needed a little help from his guardian angel Clarence to appreciate his blessings by way of seeing what the world would have been like had he not been born.

Philip Van Doren Stern wrote the original short story in 1939 and shared it with his friends. He called it “The Greatest Gift.” This is a brief story of my wonderful life, how I got to where I am today, and after some introspection, three career tweaks that I wish someone had shared with me when I started my career 28 years ago.

I’m not George, But I am a Lucky Man

My recent 49th birthday is the inspiration for this story. I have to confess I was a bit blown away. First was the realization that I was only 365 days from 50th birthday. Although I don’t feel a day over 38 and my brain still thinks I’m a spry youth, my body is beginning to laugh and tell my brain to slow down. And I have no idea whom that old man is staring back at me in the mirror. I’m learning (slowly) not to fight it and accept the inevitable passage of time.

I celebrated my birthday with my wife and kids by driving a couple hours north of San Francisco to spend three days on the Northern California coast. I love this area for its rugged beauty. Along with the Sierra Nevada mountains, the coast of California is where I seek solitude, inspiration and renewal. It is my refuge. My safe harbor.

On our first evening we looked out on a gorgeous sunset over the Pacific. In the magical light of dusk, Julia, my wife of 25 years, and I walked a trail along the bluff while our teenage kids stayed a safe distance of 200 yards ahead of us. I looked at my three daughters frolicking and laughing, and a thought came to me:  I’m the luckiest man alive.

This wasn’t an epiphany. I strive always to be grateful for everything in my life. With all the bad going down in the world, my good fortune seems more amplified as of late.

The next day I took a solo run along this same bluff side trail at sunrise, and rather than listening to one of my favorite podcasts, I decided to reflect.

Thoughts flooded my brain. At 49, I’m probably halfway through a life full of seminal moments and experiences that make me who I am. Two, in particular, came to mind: First, I won life’s lottery being born to wonderful parents who made sacrifices to advance the economic lot to which each was born and, as they started to have children, had the foresight to move to a town with one of the best public education systems in the country.

Second, the best non-decision I made as a young man launched me on the road to a successful career in one of the most gorgeous, richest places in the world. When my fiancé wanted to go to graduate school, instead of me doing a very Godley-like thing of trying to drive a rational decision-making process and analyzing options it every which way to Sunday, I just sat back and let Julia take the lead.

I encouraged Julia to follow her gut and not worry about me, as I told her that I could work anywhere. She decided on Los Angeles, California, and I was along for the ride. Similarly, her decision 5 years later to do her postdoctoral training at Stanford brought us to Northern California in one of the biggest economic booms and technological transformations of the past century. In short, I was lucky enough to ride my wife’s coattails to the epicenter of the greatest explosions in technological and economic advancement ever.

As someone who prides himself on thoughtful, exhaustive decisions and being in control, it’s humbling to admit that the biggest positive influences on my career and success have been mostly out of my control.

No Regrets

By the end of my run, I confirmed that I have no regrets. I’ve done some unconventional things along the way, such as a multi year sabbatical running the nonprofit Big City Mountaineers in my early 30s. I’ve made some unfortunate investment decisions; more on that in a minute. But nothing that I would turn back the clock to change or fix.

While I have no regrets, if I could go back to my 20s and 30s, there are a few things I would do differently. They’re life tweaks, really, and these are what I want to share. I’m at an age where younger folks in the workforce are asking about my journey, seem to find some wisdom in my story and even seek me out for advice as to how they can follow my path. With this backdrop in mind, I wanted to share a few things I would do different and recommend that those a few decades my junior consider benefiting from the hindsight my aged career has afforded me.

Advice #1: Work Locally

I started full-time work after college around age 21, so I’m 28 years into my career. When I look back at my work history, it includes stints with companies based in New Jersey, Chicago, Atlanta and Denver. Even though I went to California with Julia 20 years ago, I worked for companies scattered across the country for almost two decades. This resulted in two things: I spent a lot of time on planes but more significantly, I developed a national network of contacts and companies.

We work in a global world, so what’s wrong with that? Nothing, if you don’t mind spending your life traveling (which gets old quickly). Beyond the personal toll that national travel takes, it’s really the difference between a broad, multi-location network versus one deeply concentrated in your preferred geography that is the point I’m trying to call out here. When I need to fill critical roles by tapping into my extensive network, usually the first 3 names that come to mind are not local which means they would probably never take the role no matter how many perks I tossed their way. And for my personal career advancement, the cadence of my inquiries about great jobs are national in scope rather than concentrated in where I’ve chosen to set down roots.

I’ve lived in California for 28 years, and for me, it’s heaven. Matter of fact, I was just telling some friends last week that I identify first as a Californian, and only secondarily as an American. California, and in particular the San Francisco Bay area, complements my value system by offering the most incredible combination of intellectual capacity, cultural diversity, a vibrant work environment and outdoor recreational activities to satisfy any adrenaline fix. I’m not going anywhere and have known as much for most of the past two decades.

My advice is to spend time early in your career figuring out where you want to live. What suits your values and lifestyle? Go there and start building your network. Remember, building a career is not a sprint. It’s a long, slow journey. Even if you have to start at a lower, less-exciting job to get started in the location of your choice, do it now.

Advice #2: Stick With An Industry Specialty

For 20 years I jumped from industry to industry, going wherever an opportunity took me. I went from payroll to telecommunications to health care to a nonprofit in the outdoor industry and even for a few years developing desktop virtualization software. Each move made sense individually, but the long arc and trajectory that got me here today is a bit of a mess. I was always building my core skills in sales and marketing, but with no overlap in the industries, I wasn’t creating a knowledge base that built on past experience. And that’s critical. I finally corrected this industry-hopping mistake in my early 40s when I got into the SaaS, CRM/data space. And I see 10 more years going forward with this singular focus.

I look back on my crazy, interesting career, and it’s been a wild ride. Again, I don’t regret any of it, and I know that Lady Luck showing up on my doorstep more than once has contributed an enormous share to my good fortune. But I contrast my schizophrenic industry jumping with friends who got into a particular space three decades ago and stuck with it—whether consciously or not—and I think they seem better for having done so. Yes, I’m probably more fun to talk with at a cocktail party than someone who spent the entire career in semiconductors, but there is no doubt that a single-industry focus can allow you to go farther and faster than hopscotching around as did I.

So my advice is this: If you find an industry you enjoy and that you believe has a bright future, stick with it. Build deep domain expertise. You can spend your career-enhancing your knowledge base and becoming a master in your field rather than a jack of all trades. You’ll enrich your network at the same time.

Advice #3: Never Be Afraid to Speak Up

At this point in my life, I’m known for my blunt talk and willingness to speak up about things most folks are scared to address. I’ve heard my style described as Radical Candor, although I knew nothing of the concept until very recently. My style started with an East Coast upbringing and emerged after some costly mistakes when being polite and proper did more damage than what candor might have yielded.

Back when I was in the healthcare industry, I made a costly mistake of being courteous when I knew something was horribly wrong in our startup. Despite having an amazing product, sales cycles were too slow, the market too small and the company spending far too much money dreaming that the future would be different. It ended badly with down-rounds, waves of RIFs, broken marriages and dreams and, ultimately, bankruptcy. It cost me six-figures of my own money and seven-figures of some of my dearest friends’ because I held my tongue. Had I spoken up as the water in which we swam was getting warmer, I genuinely believe I could have turned the business around and avoided disaster. But ‘it wasn’t my place’ and going above the CEO to the Board to explain the direness of our situation and fatal flaws in the business model would have created a crazy battle for power that felt disrespectful. ‘They’ll come to me at some point. They must see what’s going on’ I kept telling myself. They never did. Woulda, coulda, shoulda.

It was an expensive lesson, and I vowed never to go gently into the good night, but rather rage, rage, rage. Forever forward, I’ve been the thorn under the saddle when it’s the right thing to do. Even at my own career peril.

I think back to the lesson of George Bailey and what would have happened had he not been born. In my case, what if I’d spoken up? Could I have made things better? Could I have turned losses into wins for everyone? I’ll never really know. What I do know is that I’ve had a lot of difficult but necessary conversations in my business career in the last 10 years. And I don’t regret a single one.

I’m not suggesting you be rude or reckless. You don’t have to be a bull in the proverbial china shop. But when you see things being done incorrectly, don’t be a passive bystander. Be the elephant in the room…or at least point out the elephant in the room. And you don’t have to wait until you have a chair in the boardroom to do so.

And something more. It’s also about speaking truth to yourself in every aspect of your life. It’s liberating…believe me. I only wish I’d done it sooner. Keep in mind, too, that as difficult as you think it is to speak up when you’re low on the totem pole, it can be even harder when you start moving up, getting promotions and making more money. It’s incredibly easy to check yourself and go along to get along. But when your decisions, silence and complacency impact rent payments, car leases, retirement accounts, college education funds and other financial obligations for a multitude of others depending on you, I’ve learned that candor trumps convenience.

In the depths of his despair, George Bailey was lucky enough to have help seeing the path his life had taken and its impact relative to others in his family, business, and community. Although you’re unlikely to have the intervention and help of guardian angels yourself, hopefully, the path worn by grey-beards like me might help temper the meandering of your career journey in some small way. Richness awaits many of you. Just be sure you’re measuring it the right way.