The last several weeks have been engulfed by nothing but the election and what will come of this country, how the market will respond, or what will happen to our own bottom lines based on who wins. Welp, it’s finally over and we at least have some insight into the next four years. The rest will work itself out over time.
Instead of entrenching myself in more political rhetoric to get myself all worked up—I know reality will likely not be as bad as we expect it to be—I distracted myself with something slightly off-topic but equally productive. I picked up a new book.
A book about The Most Interesting Man in the World.
Yeah, this guy:
In his memoir Stay Interesting, Jonathan Goldsmith, who once said that true luxury is a life well lived, reminds us that a life that we hope to someday define as a success will rarely follow a straight line.
Looking back on his life—running away from boarding school, getting fired as a busboy for pretending to be a guest, saving a noob hiker from freezing to death on Mount Whitney, losing every acting job he’s ever had before landing the one that meant everything, the role of The Most Interesting Man in the World—he recounts, “My finest moments had not cost a dine, financed instead by a mix of courage, boldness, and stupidity.”
Here’s what the most interesting man in the world taught me.
When you’re first starting out in your career, it’s equally exhilarating as it is exhausting.
On one hand, you’re young and have so many possibilities.
On the other hand, the anxiety you have for the future… I wouldn’t wish this on anyone. You have so many ideas of what you should do and who you should be by a certain age. How you’ll have it alllll figured out by 30. Lol.
This is all to say, this is the perfect time to take some risks professionally.
Try a new role in your company. If you’ve got the right moxie for it, try starting your own business. As Goldsmith said in his book, “The best time to go for broke is when you’re already broke.”
I’ve seen a number of my friends and peers take the ultimate leap of faith, venturing into real estate, working to become an author, buying vending machines to fuel a gambling addiction (more on this another day), all the way to starting a VC fund.
Considering the 2022 economic environment, it was difficult to get hired by a venture capital fund, so my friend Laurent Span was crazy enough to start his own.
Laurent said, “I chose to walk away from all of that—not once, but three times—to chase the path of entrepreneurship.”
And in just a few short years, that leap of faith and unwavering dedication to helping entrepreneurs who look like us has morphed from a growing VC fund to a successful media business, and more importantly, a way to connect with peers and founders willing to trade stories and secrets to help propel you to the next phase of where you want to be.
“Introductions to people who can help you are critical, but knowing how to handle them properly can change your life.” – Goldsmith.
He said to me, to keep yourself sane from leaving the comfort of job safety and income stability you have to have an element of optimistic delusion.
If you fail (which, in some aspects, you inevitably will), you have so much time to bounce back or pivot to something more stable. The older we become and the more responsibilities we begin to accumulate, the less we can afford to leave that stable position in the first place.
“And if you’re in your mid-20s, like I am, I believe it’s one of the least risky times to take the plunge. You have time on your side, fewer family or financial obligations, and the flexibility to bounce back if things don’t go as planned. It’s a time when you can afford to experiment, fail, and try again—less tethered to the constraints that might come later in life,” Laurent tells us.
I know it’s so much easier said than done, but don’t overthink what will happen next.
So many people are afraid of failure or the optics of failing. But the truth is, no one will care or remember your shortcomings as much as you will. The average person is thinking about themselves. I’m thinking about myself thinking about myself just writing this post.
Having a lot of money when you’re young sounds like the dream, right? We crave financial security because when money is low, things get scrappy but can also cause anxiety to compound on itself.
Don’t get me wrong, saving for retirement or financial freedom is important.
However, if you never take career risks and opportunities because you’ve already mapped out how much you’ll need to earn to fit into some preconceived idea of reaching your number, it will only lead you down a one-way road with no outlet.
Burning out, realizing you’re stuck in a place doing something you no longer enjoy, or watching as outsiders get promoted above you because they had experiences in other areas you didn’t. To me, that’s not a way to live and a surefire way to make you quit anyway.
Sam Ro, a great example of this, shares his experience of how his substack TKer came to exist:
Sam ended the original Tweet with, “Things have not been linear.”
He was really good in his audition, apparently, but Dos Equis was thinking they might want to go younger. [Jonathan] Goldsmith was nearing 70 when he auditioned.
But his agent, upon hearing this objection, said: “How can the most interesting man in the world be young?”
As Goldsmith put it: “Her rationale made sense. To be interesting, you have to have experiences. And to have had experiences, you needed time. And I had spent a lot of time having a hell of a time.”
“Let me call you back,” they said.
He got the part.
Goldsmith writes on his success:
“If I’m being honest, I wish this all hadn’t taken so long. But, then again, maybe if success had come earlier it wouldn’t have meant as much as it does now… The harder knocks, disappointments, and travails one has, the more opportunity one has to gain awareness of who the devil we really are. I’m still trying.”
Cherish those experiences, even the “bad” ones. They taught you something. And they will make the later successes taste all the sweeter.”
If you are in your mid-career, the choice between keeping your mental sanity in check and paying the bills can weigh heavily on you.
The same principles can still apply to you: start sooner rather than later, but now it must be with purpose.
I tell clients facing a fork in the road to seriously weigh the pros and cons. This means making a list of each option’s potential benefits, drawbacks, salaries, time, and expected commitments and considering both the short-term and long-term implications.
Financially, it would be wise to have at least a year’s worth of your core living expenses set aside and a solid business plan for how you expect to make a profit.
Do your due diligence, and be sure you have a floor to stand on so that paying the bills won’t be the number one thing on your mind if the transition takes longer than expected. Having an emotionally and financially supportive spouse could help make the transition that much easier.
I can’t say definitively whether it’s a good idea, whether things will pan out for the better, or whether it will be an expensive lesson learned.
Your heart will pound, and you’ll likely have restless nights of sleep. There’s nothing I could say to calm the nerves.
What I can say is, it’s never too late to reinvent yourself.
If you feel confident that you know what you’re doing—you have a business plan, the safety cushion, and the guts to do it—hold your nose and dive in.
From there, you’ll either sink, swim, or float.
Your unique experiences, even if they don’t follow a straight path, are what make you valuable and can lead to the stories you’ll tell for a lifetime.
Stay thirsty for life my friends.
