Lessons from Life, Leadership, and That One Job I Loved

Lately, I’ve found myself sitting in this funny, humbling spot, wildly rewarding spot—friends asking me for advice about what their child should do after graduating. It’s a spot where my roles as a CEO, parent of a soon-to-be young professional, mentor, and eternal student of life all intersect in the most unexpected ways.

It’s wild to think about, but in just a handful of years, my own son will be stepping into the workforce. Watching him grow has been one of life’s greatest joys, but it’s also made me reflect on the wisdom I’ve gained from my own journey and those I’ve had the privilege of working alongside.

Maybe it’s because I was raised by a parent born in 1930, twice my age, and a treasure trove of wisdom and wit I can only dream of having one day. My father’s quiet strength taught me the value of hard work, the importance of building relationships, and, most importantly, how to nurture those connections for decades. To this day, I marvel at how effortlessly he balances these things, never seeking recognition but always leaving a lasting impact.

I’ve carried those lessons into my own career, starting at Adaytum—a company that wasn’t just a workplace but a playground of professional growth. Thank you, Guy Haddleton , for creating an environment where I learned more than I ever thought possible. I was a sponge, soaking up knowledge from incredible coworkers, many of whom I’m fortunate to call my friends and mentors to this day.

Then came the years of cutting my teeth, applying those lessons, and (hopefully) leaving behind nuggets of goodness, growth for sure. For the past 10 years, Leadous has been my home—a place where I’ve been able to hand-select the most amazing people to work with. Some have flourished, creating the most amazing opportunities for themselves. And, yes, some didn’t. That’s life, after all.

So, what do you tell a college graduate, freshly minted and ready to conquer the world? Besides, run from your parents (that's for my friends reading this). What do you tell their parents, nervously trying to steer them without micromanaging? Here’s what I’d share, with a few anecdotes along the way:

1. Don’t Wait for Perfect Conditions. There’s no perfect first job, company, or role. The best lessons come from diving in, even when you feel unsure. At Adaytum, I had no idea just how much I’d grow. But I stayed curious, and that curiosity became my compass. I've had employees at Leadous share that they have gotten the chance to do way more because of the size of our company, they weren't put in a box - maybe, if it's a sure bet, go small first.
2. Learn How to Build Relationships—and Keep Them. Build it, nurture it, and never take it for granted. I call on mine to this day, and it continues to open doors I never even knew were there. Those relationships are built by showing up for others first. Your network is your net worth, they say, and it's true.
3. Ask Questions, Even the “Dumb” Ones. Asking questions—good, bad, or obvious—is how you learn, grow, and, often, make an impression. The most successful people I’ve mentored are the ones who aren’t afraid to ask. And now you can ask Google, ask ChatGPT, just don't wait. (More on that next...)
4. Take Ownership. Never wait. I just said at the Leadous annual kick-off that “‘I’m waiting’ are the words that will stall your growth and your career.” Waiting shifts the responsibility onto someone else when, in reality, you need to act, solve, or push forward. Step up, take charge, and own your growth.
5. It’s Okay to Pivot. Many people I’ve worked with (myself included) didn’t stay in the roles we thought we’d have forever. Pivoting isn’t failure; it’s finding what works for you. I mean, at one point… well, never mind. ?? The key is to recognize when it’s time to pivot and to do so with intention.
6. Learn How to Be Disliked. This one’s tough but necessary. In life and work, not everyone will like you. That’s okay. Stay respectful, focus on what matters, and let go of the rest.
7. Be the Sponge. I’ve been saying this since my Adaytum days: soak up everything you can. Every job, every role, every conversation is an opportunity to grow. You’ll never regret learning, but you might regret the times you tuned out when you could have tuned in.
8. Balance Ambition with Patience. You don’t get a corner office on day one; you earn it. And now we all want a home office in our favorite city, working where and how we want to. But careers take time, and the journey is where the growth happens. Be ambitious, but also recognize the value of sticking with something long enough to master it.

Managing people, mentoring, and raising a future workforce member have all taught me this: we need to teach young people how to solve problems, not solve them for them. Let them figure things out, even if it means watching them stumble a little. That’s where the real growth happens.

At the end of the day, whether they soar or stumble, the key is to stay curious, stay open, and trust the process. Life has a funny way of working out—and when it does, you celebrate at happy hour. Cheers to the journey! ??.