Rethinking Success

Mike Montgomery
Bootcamp
Published in
2 min readApr 18, 2023

For most of my career, I had a grind mentality: more hours worked meant more success. I took pride in working more hours than anyone else and wore it as a badge of honor. This mentality led me to have a successful career and reach my business goals in my 20s and 30s. I was able to start my own agency, become a Design Director, and work with some of the biggest brands in the world, including Disney, NFL, NBA, Google, and Montblanc. This mentality also led me to buy and sell multiple homes, each slightly larger with more equity. I felt successful, but as it turns out, being successful on paper doesn’t directly relate to happiness.

Even though I was successful on paper, this grind mentality left me feeling depressed, burnt out, neurotic, distracted, and generally unhappy. This led me to reflect on my life and ask myself: if I’ve worked this hard for so many years and have everything I want in life, then why do I feel unhappy all the time? This led me on a path of self-discovery to uncover why I felt this way.

Through this discovery process, I decided to take a step back and reflect on what success means.

What I’ve uncovered is that success is a highly personal thing. There is no general measure of success. Success for one may mean building a multimillion-dollar company, while success for another may mean getting to do the work they are passionate about every day. The key is to define what success means for you. Take time to write down what your ideal life looks like, then put a plan in place to become that person. Take small actions every day that move yourself towards that goal.

For some, this may mean redefining their definition of success. For me, success meant working less, having less stress, spending more time with family, and focusing on my mental health. Redefining success doesn’t mean that you have to discard your previous goals. It just means that you have the opportunity to reflect on what is truly important in life. By making small life changes, you can still get there, only in a better mental state.

A few strategies that have helped me are setting clear goals, creating systems, setting cut-off times, and carving out sacred hours that I will not work. I’ve learned that time away from work actually has a positive effect on the time worked. Although I’m working fewer hours, those hours are more focused and intentional. My larger goals have not changed, only the path to getting there.

Let me know if you’ve experienced this in your career.

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