The Great Contradiction
Where Advice from Successful Entrepreneurs Falls Short
As we acquire experience it’s natural to wonder what we would change or tell our younger selves. It’s all the more intriguing when the question is posed to the entrepreneurs we admire.
The one consistency I’ve found is that few advocate altering the course of their lives. The entrepreneurs we consider successful don’t wish away past events or decisions they’ve made. When asked if there’s anything they would do differently in their careers or lives, they reject the question entirely. They’re comfortable with the decisions they’ve made and the obstacles they’ve faced because it has led to where they are today.
At an individual level, this a productive, if not essential, behavior. But some of the most brilliant minds also have a tendency to prescribe their past decisions as a blueprint for others to follow–advice that’s in direct contradiction to their emphasis on the importance of making it their own way.
The reality is that there is no single path to success and it’s impossible to make the optimal decision every step of the way. But you stand a far better chance if you leverage your unique abilities and embrace the direction you find for yourself, instead of attempting to replicate the decisions of those who have experienced past success.
The Greeks defined this as euthymia. Seneca explained it best as, “believing in yourself and trusting you are on the right path, and not being in doubt by following the myriad of footpaths of those wandering in every direction.” Some will call this fate. Seneca referred to it as tranquility.
Once you trust in the direction you’re heading, you’re able to better negotiate one the most formidable obstacles you face–yourself. As you move out of your own way and out of your own head, you free yourself to make meaningful progress instead of second guessing.
It should come as no surprise that most successful entrepreneurs embody this lesson. But their unequivocal belief in themselves and their ideas often makes it difficult for them to refrain from projecting their path upon those with open ears.
Queue the contradiction–advocating the importance of your individual path and choices, then turning around and prescribing specific actions to others attempting to reach similar goals. It’s something I encounter on a weekly basis, with advisors directing early-stage startups to emulate a specific set of actions because it worked for them once upon a time.
To be fair, this seems to be a human tendency–regardless of the degree of success experienced. But pay careful attention to the next podcast you listen to when the inevitable, “What advice would you give your 20-year-old self?” comes up. Is the line drawn after relevant insight and a useful aphorism, or does it digress into advice for listeners to follow an exact sequence of events?
This is a useful way to identify the smartest entrepreneurs in the room–those who understand that their choices are their own and could never be replicated by anyone else. They accept that there is no standardized path for getting from A to B.
While it’s important to trust in your own direction, pretending like every decision you’ve made has been the optimal choice and that others might follow your exact path, is ego at its finest.
The belief that your route and your decisions were the only possible combination to get to where you are today is just not true. At best, it’s a foolish narrative we tell ourselves that takes the concept of fate too far. At worst, it’s pure arrogance. The concept of euthymia is only relevant at an individual level.
The likelihood that anyone has made the correct decision every step of the way–or that there is even a “right” decision to begin with–is an impossibility. Each one of us, including the most successful, have made the wrong move at certain points in time. And that’s okay. Some decisions carry greater weight than others, obviously you want to avoid the fatal errors. But more often than not, it’s about what you do next. What’s your next move? How can you use this decision as leverage to get closer to where you want to be and better yourself?
Success, as defined by you, is far more about resourcefulness than a checklist of prescribed actions.
There are dozens of ways to get to any single point. What’s important is your strategy for dealing with obstacles and learning from failures, not your attempts to replicate someone else’s career or life progression. The likelihood of the latter working is infinitely small and would require far more energy in attempts to exert control over random events.
The more productive route is to harness the energy from random encounters, breaks, and obstacles that are unique to your own life, and turn them into momentum.
“There are routes to success that are nonrandom, but few, very few people have the mental stamina to follow them.” –Nassim Nicholas Taleb 
This is not to say that you shouldn’t learn from the mistakes and lessons others have faced, whenever possible. But to a much greater extent, the course of your life will be determined by your resourcefulness and willingness to learn when you come up short. Sustainable success is built by having skin in the game–as Taleb advocates–and learning as you go.
Advice to follow a template of decisions should be approached with caution. The individual path and environment that worked for someone else, no matter how successful, is irrelevant to your current position.
You will never be able to replicate the lives of the entrepreneurs that you admire. But you can examine the systems and mental models that give them their competitive advantage. This is where you’ll find the truly valuable lessons that you can apply to your own life, direction, and decision making.
Do you want to build better mental models and discover the best systems that successful entrepreneurs have in place? Join my reading list and I’ll send you my top 5 book recommendations for entrepreneurs, with book notes for each so you can dig in.