Last Updated on October 24, 2025 by Chin Yi Xuan
A confession:
As a solo finance creator for the past 8 years, anxiety is no stranger to me due to the uncertain nature of my career.
Over time, I have become better at managing uncertainty. But this amazing IG reel from podcaster Steven Bartlett, who interviewed many successful entrepreneurs, helped me put things into perspective:
“Your relationship with uncertainty will define your entire life.
If you are the type of person that needs the answer, needs the branch that you’re going to swing to, the type of person that can’t jump off the tree without the branch being within reach…You’ll end up overstaying your welcome in situations that are no longer serving you.”
He further adds:
“The most successful people I interviewed all seem to have in common is they are able to choose uncertainty over certain misery.”
Isn’t this powerful?
Too many people (including myself) have chosen to stay in situations that make them miserable, be it:
- A toxic workplace
- An unhealthy relationship
- A dying business (more scarily, a slowly dying one)
It is our nature to seek ‘comfort’ in a predictable life, even when it is slowly f*cking us up.
The question: How do we build up the courage to step into the unknowns?
Managing uncertainties with ‘Stacked Confidence’
These days, I’m (slowly) learning to manage uncertainties through ‘Stacked Confidence’.
Instead of seeking absolute certainty, I stack foundations that provide me confidence to pursue paths with uncertain outcomes:
(1) Proper Risk Management: Deal with worst-case scenarios
- 6 to 12 months of emergency fund
- Proper insurance coverage
(2) Multiple sources of income
- Different streams of business income
- Low-maintenance dividend income via my Freedom Fund
(3) Continuous upskilling + getting mentors
- Pursuing my Certified Financial Planner (CFP) qualification
- Engaging different mentors, such as a financial planner and a business coach.
(4) The final piece of the puzzle is trusting ourselves.
As my business coach always reminds me:
“You’ve got to trust that you have the ability to deal with situations when they arise.”
As simple as it seems, I am still internalizing this lesson to this day.
Building courage with ‘Stacked Confidence’
One last thing:
When we seek certainty, we hope that bad things never happen.
When we ‘stack’ foundations to our confidence, we are building faith that we’ll have what it takes to come out of obstacles as a stronger and wiser person.
Hope this helps! 🙂
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p.s. If this resonates, feel free to share your thoughts in the comment section. I’d love to hear how you are building your own ‘stacked confidence’ in life!
