4 Things 2018 Taught Me About Surrendering as An Entrepreneur

In what’s normally a mad dash to the finish in the Annual “Lingering Client Deadlines and Unaccomplished Goals” Race, 2018 was different. Last year, I chose to remember that there were other routes I could take. That the year was a marathon, after all. A solo race with myself to my own personal journey.

“Take. Your. Time.” — is what the voice said as I was closing in on the final leg.

So I did.

Views from a dream trip to Marriott Resort Momi Bay in Fiji.

Views from a dream trip to Marriott Resort Momi Bay in Fiji.

Having spent the year devising a plan to build a parent company to house my businesses, coaching speakers to bring their ideas to global stages, strategizing with creative minds to help them move from idea to execution, consulting companies on redefining their stories, designing and facilitating learning experiences for emerging leaders to realize their potential, and teaching the TMAY method to artists, entrepreneurs, creative professionals and students around the world — instead of feeling guilted by countless memes and social media reposts urging me to have my shit together by December 31 (or else?), I spent the last two weeks of 2018 savoring, celebrating and soaking in what remained of an incredibly eye-opening year. And then I spent the first week of 2019 reflecting and taking inventory.

Over 45 flights. 130-ish days on the road. 80,000 miles traveled. 20 speaking and teaching engagements in 6 countries. 25 therapy sessions (shout out to Elizabeth and Zoom!). 10 successful client projects. 300+ meetings. Confronted and surmounted addiction (8 months and counting! — more on that in a future entry). Married the love of my life/best friend/business partner. Started working on a dream project with one of my favorite companies (more on that later, as well). Celebrated the first anniversary of my book. Had countless run-ins with fear and self-doubt followed by reunions with faith and courage. And a partridge in a pear tree…

It was a 365 day awakening that rocked me to my core and showed me exactly what I’m made of — the kind of might that can weather any storm. And in wanting to get closer to that magic to really manifest my dreams and live a purpose-driven life, I knew exactly what my theme for 2019 would need to be: surrender.

verb. to give (oneself) over to something (such as an influence)

I talk about it A lot. Alone. With my wife (incessantly). With friends. But the practice of it is a completely different ballgame — especially as an obsessive (read: Virgo) entrepreneur. So in my moments of reflection as the new calendar year rolled in, I wrote down the lessons I’d need to apply in order to commit to the stretching, exploration, and inquiry that this new theme would demand of me.

Here’s what 2018 taught me about surrendering.

1. God is over fear.

Fear has always shown up in the form of anxiety for me. The day before a talk, a big meeting, a class I’m teaching. Even when I know I’ve done the work. Even when it’s something I’ve successfully done hundreds of times before, fear has a way up creeping onto the scene and butting in with all the what if questions:

What if it’s not good enough?

What if they don’t like me?

What if I fail?

But in the words of the great Kimberly “Sweet Brown” Wilkins— ain’t nobody got time for that!

All those anxious questions are normally rooted in ego, dressed in the letter “I”. It’s me worrying about something I have no business worrying about. Something from a past I can’t change, a future that hasn’t arrived, or a present that I’m missing the opportunity to actually be present for. I forfeited so much time and energy creating mental chaos and making myself responsible for things beyond my control. What has zapped me out of those moments time and time again is remembering all that I do, all that I am, is about something bigger than me.

“I tell the kids and I tell proteges, always have humility when you create and grace when you succeed, because it’s not about you. You are a terminal for the Most High. As soon as you accept that, you can do it forever.” — Quincy Jones


2. Legacy over currency.

It’s no secret that one of the toughest challenges of entrepreneurship is cash flow. Last year was my human development agency’s best financial year but there were definitely valleys for every peak. From delayed team payments due to late client invoices to coming up short on revenue projections when deals fell through, no matter how tight things got financially, I had to be disciplined enough to not make decisions out of desperation or lack.

That meant only saying yes to projects I believed in with clients who aligned with our vision and values. It also meant letting go of clients who were no longer in alignment and revisiting past projects to assess the value my team brings to update our pricing so that it accurately reflected the long-term impact our work makes. Short term money will have you distracted by the allure of chasing a bag (💰 🏃🏾) instead of solving real problems.

Entrepreneurship is a marathon, not a rat race. When we made sure our focus was on impact and not money, we ended up taking on less projects than the year before and attracted true partners who were interested in working together over time.

“It’s just legacy and currency. It’s just money and how you feel. And everybody gives up how they feel for short term money. And then they try to reconstruct it later. The problem is, everything is on the record. “ — Gary Vaynerchuk


3. Create a personal learning & development plan.

If we’re lucky, we never stop learning. In fact, I believe it’s our responsibility to be lifelong learners. To accumulate knowledge and understanding about ourselves, others, and the way the world works and apply those learnings to growing and living more harmoniously together.

About 30% of my work is collaborating with companies and educational institutions to rethink and create strategy around what learning and development looks like for employees, teams and students. Specifically as it relates to nurturing their passions, uncovering and acting on their potential, and doing their best work.

I thought it was important for me to do the same for myself. So I took stock of all my goals, passions, and aspirations and I mapped out 6 focus areas where I want to learn and grow as a person and further develop the skillset and mindset to actualize my vision. Then for each of the focus areas, I did some research and compiled a list of conferences, festivals, courses, talks, trips, books, experiences, and self-designed projects and from it I curated a learning and development plan for myself through 2020.

Not to toot my own horn but 📯 — it’s a really dope plan and I’d highly recommend creating one of your own. Hit me up if you need support.

A snapshot of my “areas of study.” I keep my L&D plan in a Dropbox Paper doc and do progress check-ins 2x a month.

A snapshot of my “areas of study.” I keep my L&D plan in a Dropbox Paper doc and do progress check-ins 2x a month.

“When you are a leader, whatever you are and are not doing for yourself gets experienced by others. Others model your movements and your attitude, not your intentions, not your speaking.” 

— Sallomé Hralima


4. Serve yourself the way you serve your clients.

Creating my L&D plan made me acknowledge that I had been sitting on way too many ideas and projects waiting for the “right” time. I got so tied up serving clients that I lost sight of and had no energy left to work on the things I was most excited about.

And then I thought, what if I invested the same time, energy, creative and intellectual resources I put into client projects into my own?

Behold, a (not so) novel idea.

Behold, a (not so) novel idea.

So I decided I’d start treating myself like a client and chose a few special interest projects to work on this year. I’ll be sharing more about them in the coming months, too. And I gotta say, after taking some big L’s and experiencing some major wins in 2018, I’m really excited to apply these lessons in the new year. I mean, how blessed are we to be able to start over and do something different?

Here’s to surrendering to all that 2019 (and beyond) has in store 🎊🎉.