How I Redefined My Success by Asking These 3 Questions

When you think of Entrepreneurship, many things come to mind. Among them, I’m sure, are those big American success stories — Bezos, Jobs, Musk.

Whenever I ask my clients what brand they admire most, they usually choose Apple, Tesla or Amazon. These are all wildly successful brands, but they also have highly revered figureheads — leaders who defied the odds, bootstrapped and built massive brands from the group up. It’s what we, as entrepreneurs, all aim to achieve, right? Our faces on the cover of magazines, millions of dollars in the bank account — that’s success, right?

I heard a fascinating figure during a sermon the other day that stopped me right in my tracks. Teachers are ranked the #3 professions for American Millionaires. To me, this didn’t make sense; they’re right up there with engineers and doctors — but with notably lower salaries. How could this be possible? Research indicates it’s because they are better at building wealth slowly and steadily. They are better savers and better spenders. It doesn’t sound sexy, but their net worth stands alongside our highest earners in the US.

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This same sermon touched on an idea that has stuck with me ever since. We idolize outliers. Why? A large part of it is steeped in our American Culture. We build a country built on rebellion, and if you look at our idols — none of them ‘fall in line’ with social norms. Marlboro Man, Motley Crue, Michael Jordan, Taylor Swift, James Dean, Jay-Z — they rejected our norms. They did things their way, and it worked. We, as a culture- love that.

Every one of the amazing humans mentioned above is the exception — the lightning in a bottle. Their stories are iconic, fun and exciting — told again and again of ‘look what they are able to achieve.’ But what about the rest of us?

The outliers give us hope. They let us dream and aspire. But when we’re looking up, we’re not looking around; we have blinders on. And that is what I want to talk about today.

Success is such an arbitrary concept. It looks different for everyone. I used to say the cover of Forbes was my definition of success — and while that would still be awesome, I no longer feel like I need the validation of a magazine cover to feel accomplished.

For me, there are 3 questions I asked myself that really helped redefine what I wanted from my business and what it would take for me to feel truly successful:

1. Who are your idols and why?

When I think of the ultimate entrepreneur success story, I think of my girl Taylor Swift. Not only because I am a fan of her music but also because she created an incredible culture around her brand while completely redefining her industry and never compromising on her values.

I look at her decisions and feel inspired to carve my own path as well. I look up to her not because of her popularity but because of her integrity and wise decision-making. I also think about my mom and grandmom, who were two undeniably strong women who helped pave the way for me to be here, and I am writing this article today.

Sometimes, the going gets rough, and I feel really down. In those moments, I think about the people I look up to. I try to see myself through their lens, and I ask myself how they would see me in that moment. It’s a powerful reframe that helps ground you back in what matters. Lastly, and this may sound strange, I think of the younger version of myself. The 10-year-old version of myself, the 18-year-old me. I ask what she would think if she could see me now. I know the answer: she’d be proud as hell.

2. What are your core values?

The concept of values in business is such a double-edged sword. Every brand has them — but how much do they live in them? Are they just words on a sheet of paper? The same goes for you as an individual — and I argue the values you have as a human should be 100% aligned with your values as an entrepreneur.

In times of doubt, my value system acts as my north star. Say I lose a huge client. Obviously, it sucks. But if I ask myself, ‘Was I authentically myself?’ and ‘Was I creative, and did I provide outside-the-box solutions?’ and ‘Did I do my best?’

If the answer is yes, I can walk away with my head held high. I can go back to the mindset of ‘this or something better’ and know that one thing is leaving to make space for something bigger. Most importantly, I can separate myself as a person from the business I created, knowing it’s not personal.

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3. What legacy do you want to leave?

One of my favorite poems is “What is Success” by Ralph Waldo Emerson. In it, he describes so many ways to be successful — like winning respect, earning affection and laughing often. Some of the things he describes are not even on the radar of our current ‘goal-getter’ mentality, which we tend to measure with extra zeros in the bank account and more accolades for our LinkedIn.

He ends the poem with some truly profound lines: “To leave the world a bit better, whether by a healthy child, a garden patch or a redeemed social condition; To know even one life has breathed easier because you have lived; This is to have succeeded.”

I often think about this in terms of the legacy I want to leave in this world. To me, it’s about more than making more money or getting all the awards. I spent so long chasing that, and it was so empty. Everything changed for me when I started thinking about impact.

How can I use my gifts to make this industry, my community and the world a better place? If not this- what’s it all for? When I measure success by legacy and impact, I am working for more than myself. It matters — and I can work with clients to make their work matter more as well. It made me dig deeper and re-lit the fire within that was running on fumes from burnout.

I get lit up talking to any entrepreneur about their business and why they created it. I love hearing their dreams and desires. I also cringe when I hear, “I want to be the Apple of [Insert industry here]. It’s great to aim high and have idols, but it’s also great to define success on your own terms. Why Apple? Is it because they’re such a branding giant? Or is it because you value their innovation? Let your values and impact become your baseline, using your idols as a gut check and guide. That is to have truly succeeded.