Confidently Lost - Navigating growth when you don’t have all the answers
The concept of uncertainty to me is fascinating, especially because it’s so often roped together with anxiety. I have always equated certainty with confidence.
Uncertainty is uncomfortable. And being certain gives me strength. That's the equation. At least that's how I see it.
Why this fear? Whether it’s business, a career move, a new skill, or a fitness goal, I want assurance that my efforts will pay off. The “efforts should pay off” part causes anxiety. This assurance of a predictable, desired, and safe outcome makes uncertainty unpleasant. And I think it's safe to assume most people are on the same page.
99% of people would rather be uncomfortable and unhappy than uncertain.
This is the truth and it’s an interesting truth at that. I have always wanted to be “certain” because I thought that would give me strength, but there’s more to this here. What if we had a framework to navigate growth through all the uncertainty?
Changing your mindset around Uncertainty
Decision-making bias and focusing on the process
I think understanding the roots of uncertainty and our thought process around it could immensely help our cause. Annie Duke - a former professional poker player and decision strategist - has a brilliant way of turning the tables on our instinctive need for certainty.
She talks about the concept of “resulting”, the tendency to judge the quality of a decision solely by its outcome, in this episode in Preston Pysh’s podcast.
Annie Duke: Just tell me like in your gut what this feels like. Somebody sets you up on a blind date. It's the worst date that you've ever had. Does it feel like that was a good decision?
Stig: No, that would feel like a horrible decision to spend the night not out with that blind date.
Annie Duke: Okay somebody set you up on a blind date and it goes great. The person is the love of your life and you live happily ever after. Does it feel like a good decision to go out on the date?
Stig: Yes this definitely feels like a great decision.
Judging our decisions based solely on their outcomes is an all-too-common habit.
You know the probability of heads or tails after flipping a coin is 50/50. But nothing will tell you the “result” or the outcome of the next flip.
Outcome-based thinking is often misleading. Outcomes of a decision or action are often affected by variables beyond our control, from timing, to luck to market conditions, you name it. This black-and-white thinking often keeps us stuck, anxious to try new things for fear they might “fail.”
Understanding this can liberate us of the anxiety of uncertain outcomes. Because the true measure of the quality of your decision is the robustness of the process - the work you put in. Success is often less a direct result of skill and more a combination of skill and factors beyond control.
The Dance with uncertainty
People who are so certain of the future, who know exactly where they're going, who have a very clear idea about where they're going to be in two or three years, I often say how boring.
Robert Greene talks a lot about uncertainty in his books and videos. In his video “The Dance with Uncertainty” he talks about balancing uncertainty. Being on the extreme end of the uncertainty spectrum could be crippling while being on the safe side (being too certain) would be boring. Some amount of open-endedness about life and the future adds spice and it's that bit of mystery that makes life interesting.
He touches on the fact that the little bit of uncertainty has to be coupled with a sense of direction. Creating this dance and knowing where to head (in work or life) while being open to things happening is healthy.
Strategies to navigate uncertainty
I have been on the extreme end of the “uncertainty” bandwagon for quite sometime in the last few years with major shifts in terms of my career. From being a dentist to an entrepreneur to transitioning to tech, I have dabbled a lot and things have been tumultuous in terms of excitement, uncertainty and anxiety.
I have experimented, made mistakes and iterated over many frameworks to move on and help myself grow despite the uncertainty. You see uncertainty without the right mindset can be crippling and I did whatever I could do to get myself into the right mindset so I stay healthy.
Thinking in bets
Duke’s concept of “thinking in bets” gives us a simple, effective way to approach decisions without getting bogged down by outcome anxiety. When you think of each choice as a “bet,” you stop thinking in black-and-white and start considering probabilities and potential. This method opens up new ways of thinking.
Instead of “I have to succeed,” we shift to “This has a good chance of working, but I’ll still learn if it doesn’t.” This helps you develop what psychologist John Keats called “negative capability”, the ability to remain adaptable and resourceful in uncertain situations. With negative capability, we open ourselves to greater creativity, resilience, and growth.
Ask yourself,
“What’s the likelihood of different outcomes?”
“What’s within my control to influence these outcomes?”
“What’s my backup plan if things go differently than expected?”
Evolving and growing through Talent/Skill stacking
“Talent Stacking” is a concept coined by Scott Adams, creator of Dilbert Comics. The act of building complementary skills is a great approach to adaptability. By cultivating multiple, complementary skills, you’re better equipped to navigate unpredictability. Each new skill creates this synergistic effect, amplifying the effectiveness of your existing skills. Diverse skills give you the profile to approach a problem through multiple lenses, make you adaptable and help you “think in bets”.
The Six Month Rule
Josh Linkner talks about this interesting but powerful concept regarding the approach one could take towards skill-building: the six-month rule. Whether it’s getting in shape or becoming knowledgeable in Asian currency fluctuations according to Linkner, a solid 6 months is good enough time to achieve remarkable progress (in most cases).
Think of the person you want to be six months from now….With this new six-month vision, reverse-engineer what you need to learn today in order to enable your vision to materialize. Six months at a time, you'll consistently marshal yourself and your company to your own field of dreams
You don’t need to commit to a skill or goal for a lifetime to see results. You could frame yourself around this time bound consistency. Setting manageable goals and seeing consistent progress within a six month block helps you get through overwhelm and uncertainty.
Be consistent and celebrate small wins
Rather than pushing for maximum effort each day, moderate yet consistent efforts yield sustainable progress. Billy Oppenheimer provides an excerpt about how Kobe Bryant viewed progress - ‘“I wasn’t the most athletic,” Kobe said. “So I had to look long term…I had to say, ‘Ok, this year I’m going to get better at this. Next year, that. And patiently, I got better and better. It was piece by piece. It was the consistency of the work. The consistency of the work,” he stresses. “Monday, get better. Tuesday, get better. Wednesday, get better. You do that over a period of time—three, four, five, six, seven, eight, nine, ten years—you get to where you want to go.”’
Over time, small wins through consistency build a resilient mindset and reinforce our belief in our ability to grow. Small, consistent steps make all the difference.
Closing Thoughts
For me, mitigating uncertainty is all about building a healthy mindset, taking action, having skin in the game, seeing the results of my work and building confidence. All of this builds resilience. Overcoming uncertainty isn’t about knowing every answer or eliminating risk. It’s about showing up consistently, learning from each step, and building a life that thrives on the unknown. Uncertainty can be a powerful catalyst that, with the right approach, will help you grow stronger, more adaptable, and ready for whatever comes next.