Letters to my 22 year-old self - Part XXIV - "Beyond Titles and Paychecks: Finding True Fulfillment"

“To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment.” – Ralph Waldo Emerson

Dear Shawn – You are 22 years old and bursting with energy and ambition. You’ve got a plan: work hard, earn the promotions, collect the accolades, and one day, you’ll define success. You’re climbing ladders, chasing titles and counting paychecks because you’ve been told that’s the formula for happiness.

But sitting here approaching 50 years old, you have learned a lot. Specifically, that success as it’s traditionally defined, can be a hollow victory. The accolades, the fancy title, and even your bank account balance may look good to others, but they can leave you feeling empty if your work isn’t rooted in something deeper—something that allows you to do your best work, is inline with what you value, and one that allows you to fuel and feed your soul.

You’ve learned a lot in 25 years of mistakes, moments of clarity, and finding the courage it to redefine what success truly means to you. Let’s explore this further.

The Illusion of Traditional Success

At 22, success felt like a straightforward path. You imagined a life where your hard work would naturally lead to happiness. 20 years ago your first management promotion felt great, the salary bump was very exciting, and the validation from others was intoxicating. By all accounts, you had “made it.” But after the initial adrenaline rush, you felt drained. Why? Although you did not realize it at the time the corporate culture you were in was not congruent with your values. You were surrounded by people who didn’t truly respect each other and although you weren’t aware of it at the time you were unable to connect the work you were doing with the life you wanted and the people you wanted to be spending it with.

Why Fulfillment Is the Missing Piece

While it’s easy to push aside “fulfillment” as a buzzword— you’ve learned that is actually the foundation of a meaningful career. It’s what happens when your strengths, values, and environment align. Without fulfillment, even the loftiest achievements will feel empty.

I think back to what I wrote to you in Part IX of this series, “Go All In on the Things That Matter Most.” Ultimately, success only becomes meaningful in the long-term when it’s tied to impact—when the work you do resonates with what’s important to you and take you closer to not only your professional goals but also your personal goals. In the scope of 30+ year career your efforts have to not just challenge you and sometimes even scare you, but also energize you as an extension of who you are and what you want to be.

So, early in your career take the time to ask yourself:

What truly matters to me?
What are the non-negotiables that I need in my life to truly give me a sense of solace and a strong connection to the people around me?
Am I working in a place where I can thrive and learn from those around me, or am I just surviving and trying to out-perform them?
Do I wake up energized by what I do, or do I feel like I’m just trying to find the energy everyday and going through the motions?

The Role of Culture: The Invisible Force Behind Success

In Part VII, I emphasized the importance of anchoring your career in your towering strengths. But even these towering strengths can wither in the wrong environment. Why? Because culture is an invisible force that either nurtures your strengths or stifles them.

Culture isn’t just the perks of a job description or the company values listed on a website. Culture is the air you breathe at work— what is tolerated day-to-day and how decisions are made, how people treat each other, and what behaviors are rewarded.

Let me challenge you:

When you’re considering a new role, don’t just ask about responsibilities or compensation. Ask about how the company defines success. Ask how failure is handled, how collaboration is encouraged, and how leaders walk the talk. Ask about how new entrants have found success by leveraging the people around them?

The right corporate culture amplifies fulfillment by giving you the freedom to work in alignment with your values and the way you do your work best. A toxic culture, no matter how financially rewarding leads to disloyalty and disappointment.

Culture forms the basis on which you build relationships with those around you and the leaders you look up to. The relationship you have with your direct manager is the closest you can get to looking your corporate culture directly in the eye.

The Courage to Redefine Success

In Part VIII, “Do You Choose the Red Pill or the Green Pill?” I asked you to confront the choices that shape your path. Choosing fulfillment over traditional success is like taking the red pill—it’s the harder, less glamorous road. It demands courage and quieting the “monkey on your shoulder”.

Yes, It takes true conviction to walk away from something that looks good on paper but feels wrong in your gut. It takes strength to say no to opportunities that misalign, even when they come with shiny perks and glamorous titles. But every time you make a choice rooted in alignment—with your values, strengths, and the culture you want—you build a life that feels authentic.

Redefining Success: What Greatness Looks Like

In Part VI, I wrote about the importance of defining greatness on your own terms. Here’s what you’ll learn over the next 25 years: Success isn’t about climbing higher; it’s about climbing the right mountain and taking the views along the way.

It doesn’t mean giving up on your ambition—it means redirecting it; focusing it on the impact you can make, the values you live by, and the legacy you leave to those who you’ve impacted along the way.

For you, success comes down to the relationships I am able to build, the people I have found time to mentor, and the meaningful work I do. Most importantly, constantly reminding yourself of how professional success is tied to personal success at home.

Take a moment today to do this simple exercise:

Write down three things that bring you the most fulfillment in your life—inside or outside of work. Things that really make you feel connected to the world around you.
Write down the aspects of your current role that energize you and the ones that drain you. Audit your calendar and breakdown how much time you spend on each of these activities in a given week.
Write down all of the things that you would focus on if only you had more time
Compare the three lists. Are they aligned? If not, what’s one small change you can make to bring them closer together?

Reflection like this isn’t a one-time thing. Make it a habit, and you’ll find clarity about where you are and where you want to go.

A Final Word

Shawn, success isn’t the problem. The problem is letting someone else define it for you! It’s about finding a culture that supports your strengths, choosing work that aligns with your values, and building a career that reflects who you are. Although it took 25 years, you have been very fortunate to find a career and a company that allows you to do what you do best and to do it in a way that directly drives fulfillment in your personal life. You feel balanced, supported and inspired to do you your best work and you feel the effects of this in your life every single day.

If there’s one thing I’ve learned from writing these letters, it’s that your career isn’t a single decision. It’s a series of moments where you choose alignment over convenience, courage over comfort, and fulfillment over approval. Those moments will define your life. They’ll be the reason you’re proud—not just of what you’ve done, but of who you’ve become.

If you enjoyed this write-up here are direct links to the rest of the series.

Part I – “Keep an eye on the gas gauge”

Part II – “What’s the worst that can happen?”

Part III – “What’s the ONE THING”

Part IV – “Navigating the ups and downs of a career in sales”

Part V – “Don’t eat the marshmallow”

Part VI – “Not every mountain is Mt. Everest!”

Part VII – “Anchor your career with your towering strengths”

Part VIII – Do you choose the red pill or the green pill?

Part IX – “Managing your Monkeys”

Part X – “Attacked from Within”

Part XI – “The mirror does not lie….”