Ten years ago this week, I left my role at Macalester College. At the time, I wrote that I wasn’t leaving something — I was moving toward something. I had a plan. And as we know, plans often seem hilarious when viewed in retrospect. Six months later, I shared 10 lessons from that early transition.
Now, 10 years into full-time independent work — as a speaker, coach, and consultant — it feels like the right time to reflect again. Things evolved – me, my job, higher ed, the world. It has been quite the journey. The lessons have deepened, evolved, and taken on new meaning.
1. The Decision Is the Hardest Part
Leaving my role wasn’t easy. It took courage to leave a well-paying, salary job with benefits for the unknown, especially with a family that included two young kids at the time. That decision was the hardest part. Even the most difficult challenges have been easy by comparison. The hardest part wasn’t the work or building something new — it was the leap.
2. Lonely and Alone Are Not the Same
Although I often work from home or travel alone, I rarely feel lonely. Loneliness is not being alone; it is the sense that you should feel a connection and do not. Honestly, I felt much more alone at Macalester, surrounded by so many people, but not feeling the connection I thought I should have. Solitude can be generative, and connection can be intentional.
3. Time on Task vs. Quality Output
In many organizations, time on task is equated with productivity and commitment, often involving long hours, packed calendars, back-to-back meetings, and working on actual tasks nights and weekends. I remember how busy I felt in a director role. I’ve learned to value and measure quality output over time on a task. It’s easy for me to push myself to grind away, but that rarely leads to insights, creativity, or visually appealing results. Usually, the best ideas occur while folding laundry, doing the dishes, or going for a run. I’m trying to organize my day like a songwriter with an album deadline, needing to create something new each day.
4. Learning
I love to learn. I’m constantly learning from podcasts, audiobooks, webinars, articles, and other resources to build my expertise and generate new insights and ideas that serve my clients. What I did not anticipate is how much learning I would do just to run a business: which apps are best and cost-effective, why is my website showing this error and what do I do about it, how do I work with Canadian clients to manage payments as efficiently as possible, what does this threatening letter from the IRS mean – is it real? Running a business on your own means there are no experts to turn to, and you must learn it yourself or hire someone for their expertise. I’ve come to love the learning curve, even when it’s steep.
5. Unlearning
Alongside all that new learning came necessary unlearning. I’m still unlearning grind culture, scarcity thinking, the busy disease, and a constant sense of obligation. We’ve all been very well mis-educated – me included. I’m still working on unlearning the myth that overwork equals value, and embracing rhythms of rest, reflection, and re-centering for creativity, generative thinking, authentic connection, and presence.
6. Comparison
It’s easy to scroll through others’ wins — promotions, book launches, media appearances, and huge contracts — and feel like you’re behind. But over the years, I’ve learned: comparison is the secret to unhappiness. Rather than seeing other folks doing similar things as competition, I’ve learned to think of them as colleagues. How can I learn from them, help them out, connect and partner, and cheer them on for their successes?
7. Grace and Discipline
Working independently requires both grace to be patient with yourself and discipline to keep pushing when you’d rather not. I struggle with this balance on a weekly, daily, and hourly basis. I’m still working regularly on being a compassionate boss and an accountable employee to myself.
8. Partnerships
While I work independently, the right partnerships are everything. Some collaborations haven’t worked out — and that’s okay. However, when I’ve found complementary alignment, drama-free collaborations, and genuine connections, the results have been better, and the journey has been a joy.
9. Make Plans, Enjoy the Journey
I love a good plan. And nothing ever goes as we plan. A good plan gives me the confidence to work with the unexpected and improvise in alignment with the purpose. Some of the best parts of my work were things I never planned for, expected, or would have even hoped for 10 years ago. I’ve learned to map out a plan, but also be open to, embrace, and even count on emergence.
10. Being Your Own Employee
Many ask, “What is it like not having a boss?” I often respond, “I have one. It’s me. We are working on our relationship.” Twin Cities musician Dessa once tweeted that the experience is less like being your own boss and more like being your own employee. I’ve had to learn how to lead and be led by myself. That means checking in, setting boundaries, offering support, giving feedback, and holding firm.
Gratitude
Ten years ago, I would never have imagined what this job would look like now. I wanted to live in greater alignment with my purpose and values, to offer more to the world, and be the best father I could to my daughters. I’ve gotten coaching certification, given a TEDx Talk, launched a podcast, written three books, and collaborated with some incredible people. The work I am doing is quite different from what I had hoped, and I couldn’t be happier about how it has evolved.
Today, I am working to empower better tomorrows for us all through better leadership, learning, and equity. Through my speaking, writing, coaching, and consulting, I get to make a lasting impact far beyond my direct reach.
Thank you for being part of this journey — whether you’ve been with me since my time at Macalester or we’ve just connected recently. Each connection, comment, email, outreach, and virtual coffee is rewarding, meaningful, and appreciated.
If any of these lessons resonated with you, I’d love to hear which one — and what lessons you’re learning in your own journey.
