When People Doubt You, Just Keep On Winning

When People Doubt You, Just Keep On Winning: Tips For Overcoming Your Doubters

After 10 years of grinding away, one of my friends sold his business for $73 million at age 32. It was a bootstrapped business, so he ended up getting over 80% of the gross proceeds. Can you imagine? Wow.

When I asked him what he did with his newfound riches, he said he took a month off to go surfing with his buddies. After he got his fill, he then started a new software business.

When I asked him why he decided to get back into the grind so quickly, he responded, “I want to see if I can go do it again to prove to everyone and to myself that it wasn’t a fluke.

During my financial journey, I’ve met so many people who have done extraordinarily well, yet continue to work all day and night because they know they were extremely lucky to have achieved their success. By replicating their success they also eradicate their guilt.

Their work ethic and self-awareness are both inspiring and concerning. But I empathize with my friend because I have the same desire to prove my doubters wrong all the time. It’s in my DNA.


Once You Repeat, Nobody Will Doubt You Again

Let me share my latest story of ongoing doubt and eventual victory.

During my first year of coaching high school tennis, we got to the division finals and lost 2-5 to a school three times as large. At the time, my school had never ever gotten that far in its history.

My tennis friends ribbed me, saying it was a fluke that we had gotten to the division finals. After all, the division has 70 schools located throughout Northern California. To be one of the last two schools standing was surely luck.

I agreed with them because when you come in second, you might as well have come in last. We barely won in the semi-finals. I truly believed we got lucky to get so far.

Then in my second coaching year, we won it all and beat the team that had beaten us the previous year 4-3. This was our first division championship in school history and it felt amazing to be a part of this success.

My tennis friends continued to rib me, however, saying our victory was still a fluke. I had my doubts it was all luck for us to get through the gauntlet. But I agreed with them. After all, there’s always a first time for everything.

To think I had made even a speck of difference in the lives of the kids and the program would have been an arrogant assumption. I was just in the right place at the right time.

Then in my third year of coaching, we successfully defended our title and beat a powerhouse team 4-3 in the finals. Their #1 player got recruited to play college tennis and their #2 player is a 5-star recruit as a freshman. None of my seniors were college-level recruits. But we had good depth, great team chemistry, and maybe even some good coaching.

2019 was the second division title in our school’s history. Defending a championship was harder than becoming a champion for the first time due to heightened expectations. It was also more stressful because we all wanted to prove that we weren’t one-hit wonders.

After the second division title, my tennis friends unexpectedly stopped ribbing me for coaching high school tennis. Apparently, they have finally acknowledged I may have played a part in the victory as a coach. One even asked if I could hit with his middle school son and give him a recommendation.

My friends now even ask me for some tennis tips. Of course, I just beat them up on the court instead and make them buy me beer after for losing. “Here’s my tip for you today buddy. If you played better, you would have won!”

Ah, winning feels so satisfying!

Oh yeah. I almost forgot to mention I got a lot of ribbing and worse on the internet too.

When the Internet Retirement Police this season said I wasn’t allowed to consider myself a high school tennis coach for the past three years given I have Financial Samurai and retirement income, I used their disapproval as motivation to write a new post.

This post was called, How A Tennis Coach Provides For His Family In Expensive SF. It was picked up by several major news outlets and as a result, boosted Financial Samurai’s traffic to an all-time high that month. Not bad for a coach. I’m thankful the IRP has helped me stay retired from the corporate world for a little while longer.

Maybe I’m just hardwired differently. But people’s doubt gives me so much enthusiasm and energy! There is always a positive angle to everything. It’s up to you to find it.

When people doubt you, just keep on winning. How to overcome doubters in your life.

Keep Creating Small Wins

When you attract doubters in your career, your business, on the playing field, or in your personal life, all you’ve got to do is recreate your victory to hush up your doubters.

But more importantly, once you do it again, you’ll hush up your greatest critic: YOU!

You will develop a tremendous amount of self-confidence to tackle many other things. In other words, your self-confidence is scaleable.

When I was a hiring manager, I always wanted the candidate to tell me a story of adversity and triumph. I’m a sucker for these types of situations.

It didn’t matter how small the triumph was, like winning a July 4th softball tournament. I knew that someone who consistently achieved small wins could easily create big wins for the firm.

The same goes for all of you on your journey to financial independence and doing what you want with your one and only life. Paying off a car loan might be a small win. But once you do, you will feel empowered to pay off your student loans and then your mortgage.

Once you develop one passive income stream that generates enough to pay for your monthly gas bill, developing another passive income stream to pay for your monthly food bill is all but an inevitability.

Don’t discount your small wins. Create more of them. Your small wins will snowball into greater victories.

Finally, remind yourself that you don’t need someone else’s approval to go after the things that bring you joy. Yes, losing stinks. But more than the pain of failure is the regret you will feel for having never tried.

With enough courage and determination, sometimes you might even find yourself winning it all.

Happy Memorial Day weekend to all our veterans and family members.

Readers, what is an example of one win you recreated to prove to yourself and to others that your first win wasn’t a fluke? What are some small wins in your life that helped you create big wins? Why do you think there are doubters?

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