I Talked to 8 Entrepreneurs On How They Discern Reflection from Regret

“I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying” — Jeff Bezos

It’s simple: Business requires risk.

Business requires risk, and risk requires tough skin. Because no matter how we define failure, it’s sure to happen a few times on our journey to success. And to reach success, we need to be willing to try and try again.

We’ve all discussed the benefits and bravery of getting back up again after we stumble. The Japanese have a saying for this concept of resilience: “Nana korobi ya oki” (meaning “seven falls, eight getting up”.)

But what no one talks is the interval between the fall and rise. The moments when we realize we’ve fallen. When we muster the courage to raise our eyes and survey the damage. When we push ourselves up, dusting off our forearms and knees and adjusting our disheveled hair. When those initial waves of embarrassment and shame hit…hard.

In those moments following utter failure, no one talks how to approach the temptation of regret and the painfulness of reflection. And, in our attempts to make sense of our mistake, no one talks about how they confuse easily.


Yesterday, I read an article in which someone said, “We study our pain.” Honestly, that’s what I’m doing right now. I recently failed big time and have since studied how others have faced and fixed their failures.

Below I’ve spoken with eight entrepreneurs about how they discern reflection from regret, how they’ve remedied failed business decisions, and how they encourage others to do the same.


Laura MacLeod is the founder of From The Inside Out Project®, a HR development program that fosters self-awareness and interpersonal skills.

As a business owner, social worker, and therapist, Laura acknowledges that both reflection and regret have their place. When she feels disappointed, deflated, and frustrated, she shares those feelings with a trusted friend or colleague.

“Working through these emotions allows you to examine and evaluate the situation to learn from and let it go. Pushing it aside or swallowing it (to “look on the bright side”) won’t work. Only bitterness will follow,” she says.

Laura has learned from experience that pitfalls, missteps, and blunders are part of the journey. “The tough part,” she says, “is learning how to deal with it, forgive yourself, and find a way to stay the course.”


Abhi Lokesh is the CEO and co-founder of Fracture, a photo service that prints images on glass.

Abhi has come to realize that no single negative event or bad decision can make or break a business. “Since it’s your own business, every decision and event is going to seem massive, like it’s a make-or-break deal,” he says. “The truth is, starting a business is a series of mistakes, redirects, stumbles, and hard-earned lucky breaks. The fate of your business comes down to how you respond to those events.”

Once his perspective changed, he’s realized that each event should be evaluated as a data point or experiment. Now, he doesn’t have time to wallow in regret and self-pity.

“There is always something useful to learn and gain,” he says. “Yes, even from that steaming heap of rubble that was the negative event.” Over time, he’s learned to extract those useful lessons, crystallize them, and use them to prepare for the next business decision coming his way.


Daisy Jing is a YouTube vlogger and the founder of Banish, a multi-million-dollar beauty company.

To Daisy, the hardest part of running a business is keeping her expectations and reality aligned. The most heartbreaking part is working so hard to only realize her business didn’t materialize the way she envisioned. To keep herself mentally positive and disciplined, she sees everything as a learning experience and keeps her expectations low.

“Understand that your business has its own journey; don’t compare your journey to someone else’s highlight reel,” she says.Don’t be frustrated when things don’t happen the way you expected. It’s not the end!”

She also encourages entrepreneurs to expect mistakes and learn something from every experience.


André Gauci is the CEO and co-founder of Fusioo, an online database that manages company workflows.

To learn from his failures, André continuously performs self-assessments. Through this, he’s able to determine the cause for each failure and take steps to prevent it from happening again.

“Opening up to someone else is usually one of the best ways to gain an unbiased, outsider’s perspective,” André says. This is why seasoned entrepreneurs, like André, advise prospective entrepreneurs to find co-founders, advisors, and mentors.


Ellie Shoja is the founder and CEO of Embold Media, a full-service production company.

Ellie believes that it’s impossible for a business to fail. Starting a business allows people to take part in the act of creation, which is the only reason she believes we’re here at all. “We are powerful creators, here to create,” she says. “Being an entrepreneur is one way we satisfy this desire.”

To Ellie, there should be no regrets in business. Being an entrepreneur means that she will make decisions, both good and bad. Sometimes, these decisions lead to financial gain, other times they create loss. But they’ve always taught her powerful lessons.

When faced with perceived failure, adversity, or bad decisions, Ellie remembers this: She cannot change what’s happened in the linear past, so there’s no point in regretting it. And, to her, reflection is only relevant until she can make note of what happened, learn from the mistake, and move on.

“True power is unleashed when we use “failure” as an opportunity to go internal. Meditation is a vital tool for anyone who participates in life on this planet,” she says. “It teaches us that we are not our thoughts, our emotions, our successes, or failures. We are infinite beings, and there is no better time to become reacquainted with our true Selves than when we have just failed.”


Prateek Sharma is the founder of MakeMyTrip, a booking site recently sold to the largest travel company in India.

The early years of Prateek’s startup were very stressful as it was hard for him to separate reflection from regret. Along the way, he learned two hard lessons.

Firstly, he only has control over his actions, not the outcomes. “We grow up on this diet of if you work hard, anything is possible,” he says, “and that can make you feel bad about yourself when you fail. It must mean that you’re not working hard enough!” The truth is that many external factors play into each outcome, and he’s teaching himself to make peace with this reality.

Lastly, he should create distance between his situation and his emotional state. Upon failure, he works to look at the situation from an outside perspective. “In meditation practice, I’ve learned to chant, I am not this body, I am not even this mind,” he says. “I use this to remind myself that I don’t have to be a slave to what I’m feeling. There’s always an option to choose a more constructive path.


DeeAnn Sims is the founder of SPBX, a creative PR agency.

Like every entrepreneur and small business owner, DeeAnn has encountered failures. “It’s the way that you pick yourself back up and forge ahead that will ultimately prepare you to take on anything,” she says.

She’s learned that it’s perfectly acceptable to take a moment and process the situation; if she’s sad about it, she lets sink in. However, she only lets it last for only a moment. As she’s resurfaced on on the other side of each failure, her motto has become: Well, now we know for next time.

“The way that you react to these setbacks is what sets the tone for either success or failure,” DeeAnn says.


David Naylor is an Executive VP at 2Logical, the world’s first and only Motivational Intelligence™ company.

In David’s opinion, reflection is one of the least used but most needed skills in today’s dynamic business world. The difference between regret and reflection boils down to two critical elements: the questions he asks and the outcomes he receives.

“Regret focuses on one question: What did I do wrong?” he says. “The outcome is that I beat myself up and carry the burden of regret from that point forward.

When David reflects on failure, he asks himself these three questions: What did I do right? What did I do wrong? What will I do next time to be more successful?

The outcome? He learns, adapts and adjusts, thus always improving and becoming more successful. With this strategy, there is no need for regret.


We all face failure differently. Some internalize it and become professionally paralyzed. Some maximize on the momentum of mistakes and push on without looking back. Bottom line, there’s a time and place for both an emotional and logical assessment of each time your stumble. Remember the advice of these seasoned business owners the next time you experience an entrepreneurial roadblock. Nana korobi ya oki.