Year in Review: 2021

Annual Review 2021
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I lost myself this year. I had a map, but it turns out it was the wrong map to follow. Thanks to what I realized and will reveal in this review, I know where I went wrong, and I’m a better person and in a better position for it. But if it wasn’t for some luck in the 2nd and 4th quarters, I may not be writing this from quite the same vantage point.

Ironically this year felt like the opposite of what it was like to have dreadlocks. Back then, some people thought I looked like a mess. On the inside, I felt like I had the keys to success. This year, what looked like a prolific year to others felt like busyness and burnout to me.

The theme for 2021 was Focus and Alignment. I largely achieved that, but at the expense of my own creativity and to some extent free will. I was lost in being busy.

The theme for 2022 will be Finding Flow but I must be careful not to over-correct in the same way I did in 2021. Finding Flow must be in harmony with Focus and Alignment all in the pursuit of creativity, connection, and happiness.

What follows is a breakdown of my year and a look forward at the next one. But first, a few thoughts on the concept of the Annual Review. I am confident you’ll find something helpful in here for your own form of review or reflection. Doing Annual Reviews and reading others’ has never failed to help me.

The Thing About Annual Reviews

Annual Reviews force you to be honest and clear about where you are and visualize in vivid detail where you want to be. In performing these activities you illuminate a bridge for yourself. The bridge is an indication of how far you need to go to get to where you want to be. But the bridge is also an incredibly useful map of the projects, tasks, and priorities for the year ahead. A map to help you close the gap.

I wish I started doing Annual Reviews earlier than I did because there were a number of forks in the road that would’ve benefited from more careful inspection. But I’m lucky and grateful to have ended up where I am and to benefit from the power of this now annual tradition to light the way forward.

A Quick Look At The Scoreboard

  1. Revenue growth: 141%
  2. Team growth: 6 humans to 12 humans.
  3. Personal growth: developed skills in marketing, sales, public speaking and making Adirondack chairs.
  4. Vacation days taken: zero.

This is the story of my 2021 in review.

The Story Behind The Numbers

The year began with a somewhat ill-fated stint working for On Deck which started as quickly as it ended. I was consumed by all things startup: growth, capturing attention, building an audience, and generating revenue was all that mattered. I was charging, building, failing, learning, relentlessly focused, but as it turns out, hopelessly misaligned.

None of those startup activities are bad in and of themselves. The problem was it wasn’t my startup. I told myself that partnering with a recognizable brand would help me grow my own and I was right, it did. But it came at the cost of self-determination and freedom over my own time.

The first bolt of luck struck when On Deck and I parted ways in the second quarter. I don’t regret my time there nor do I have any ill feelings towards them. It just wasn’t for me.

I then spent the summer drifting somewhat aimlessly, continuing a largely solo pursuit of audience building and the creation of products. I’m proud of the deliberate Visioning work I did with Robbie and Marie for C3. I’m proud of the two products I created on my own in both my $5 email course and Course of Action, but it was the second stroke of luck in the fourth quarter that opened my eyes to the real leverage I had as a business owner and entrepreneur.

Out of the blue, thanks to some 2019 writing and the resulting SEO juice, we were approached by a large HR software company to bid on a project to train their new sales enablement team. We ended up winning the largest single contract I have ever closed at Curious Lion by a margin of more than double. This gave me the courage to expand our team to 12 incredible humans who have put us in a position of strength as we enter the new year.

Most importantly, it gave me a wake-up call and the perspective I needed to see what Curious Lion, as a company and an agent for change in the world of online education for both corporations and individuals, was capable of.

At first, the wake-up call forced me to consider whether I needed to kill the pursuits I had spent most of the year consumed with. After careful deliberation, including the hiring of a business coach (Steven Wilkinson) I decided to keep both lines of business going. Curious Lion now has two divisions: enterprise and entrepreneur.

The higher purpose and vision for Curious Lion is to propagate meaningful change in the way companies and individuals learn, develop their careers and achieve their potential.

2021 feels like a windy traverse of a trail I had the wrong map for, but which ended in me finding a different peak entirely. A peak from whose position of strength I can see clearly back on the ground covered and ahead at what’s to come. Thanks to the lessons I’ve learned, I know what I need to do to grow Curious Lion and develop a culture for our team that can act as an example for all our clients.

The Detailed Breakdown

The way I like to do this is to make lists of a few important things: what I’m proud of, what I’m grateful for, what gave or took away energy and what lessons I learned.


  1. Planned, designed, marketed, launched and led a 150-person online course that generated over $350,000.
  2. Bought a house.
  3. Published 52 podcast episodes, dozens of YouTube videos and hundreds of social media posts.
  4. Joined forces with Marie Poulin and Robbie Crabtree to launch C3.
  5. Presented on stage four times at the ASU+GSV Summit.
  6. Made $10,000 from Course of Action and $10,000 in one sale from C3.
  7. Closed the largest single contract I have ever closed at Curious Lion by a margin of more than double.
  8. Been there for almost every day of my son Leo’s waddle into toddlerhood.
  9. Made a nice pair of Adirondack Chairs with my own hands.


  1. My wife, Jill, for being the most caring and thoughtful mother I could ever wish for Leo, for putting up with me, for designing our beautiful house, and for always having the best interests of our friends at heart (and knowing instinctively who are not friends).
  2. Leo, for being a bright, healthy, happy, inquisitive, kind, exploring little boy.
  3. Finding a home that feels like our castle.
  4. Our team of 12 incredibly curious lions to lead into 2022.
  5. The support of true fans from ODCC and Twitter who stuck with me when seas were rough. You know who you are, and I’m eternally grateful for your willingness to take a stand for what you felt was right.

Gave or Took Energy

  • Gave Energy
    1. Our internal team meetings – All Hands and the Learning Architect meetings.
    2. C3 Mastermind calls.
    3. Podcast conversations.
    4. Degreed LENS.
    5. ASU+GSV Summit.
    6. ODCC live sessions.
    7. Exercise.
    8. Meditation.
    9. Writing.
    10. Reading.
    11. Weekly reviews.
    12. Walks in nature.
    13. Visioning.
    14. Going to bed early (9:30pm feels like a late night for me now).
    15. Waking up early (starting 5AM Club in the new year, DM me if you’re interested in joining).
  • Took Energy
    1. Celebratory occasions where I was clearly making up for taking no vacation and may have overdid it a bit on the booze.
    2. Random calls with strangers (this was an interesting one for me, as I’ve really enjoyed these previously. I think I overdid it this year.)
    3. Back-to-back calls and recordings.
    4. Certain difficult personalities in ODCC.
    5. The desire to always feel in control.
    6. Late night screen time.
    7. Running the Twitter treadmill to watch the follower count tick over.
    8. Routine work (ripe for automating).
    9. Weekly community updates (ripe for delegating).

Lessons Learned

  1. To create a company that helps clients create transformational learning cultures, you have to have a transformational learning culture. We’re building just that, and it’s my favorite thing to watch the team integrate work and learning by embracing the process of learning while supporting each other in their work.
  2. Confidence is contagious. It’s not arrogance, it’s the sense that you’re part of a greater story that others have yet to discover, and the ability to clearly tell that story in a way that invites others to join you.
  3. I am an Active Controller on the Enneagram. I have an innate need to be in control. When used well, this helps me inspire people to follow. When allowed to run amuck, this consumes me with anxiety and stress. I thank my young son for helping me see this difference.
  4. Your parents went through unimaginable sacrifices to raise you. Sacrifices of time, energy, identity, perhaps even dreams. Be nice to them while they’re still around.
  5. When you can’t go everywhere and see everyone you would like, you learn to appreciate what you have right in front of you so much more.
  6. To achieve anything great, you need to inspire the commitment of others to support you. To do this you need a clear vision and values, and you need to know how to spot, enable and reward good people.
  7. I would be nothing without a kind, smart, resilient wife. Choosing your life partner has to be the most important decision you can ever make.
  8. The simplest times with my family are the happiest.
  9. I’m equally happy at my desk, busy with my work (and grateful for it).
  10. I value freedom of time more than anything else, except family.

From Feeling Burnout To Finding Flow

As I mentioned earlier, the theme for next year is Finding Flow, in harmony with Focus and Alignment. This pursuit will be guided by writing. It’s been the biggest difference-maker for my life and my business, and my biggest neglect in 2021.

I’ve been reading The Three Marriages, by David Whyte, and on the morning of me writing this review, I was rocked by a chapter in the book. In it he describes how a tidal gate was built in a stream to help drain a marsh behind it. What the well-intended farmers didn’t realize was the gate cut off a 100-year old migration route for thousands of chum and coco salmon. Whyte reflects on his own lack of writing poetry amidst a faculty job that was consuming him, “sensing some gate I had built,” he writes, “halting an inner migration, a tidal gate firmly closing off the creative flood, put together in a short year, by my unthinking busy hands.”

I was struck by how similar that felt for me this year.

He goes on to describe the burnout he was feeling: “I had erected a barrier inside me that let things out but did not allow them back in.”

Phwoar. Have you ever felt that?

But there is a silver lining. Drawing inspiration from the German poet Rainer Maria Rilke, he writes that “our ability to know what we want is first of all, often marked by an early and profound experience of its very absence.”

Therein lies the power of these Annual Reviews (or any reflection for that matter). As Whyte describes, “an ancient abiding dynamic of human existence is the ability of something, once fully admitted, to begin to change, and to change quite often into its opposite.”

And just when you’re unsure of exactly what next step to take, trust your instinct to figure it out. Not knowing is liberating. Not knowing stops us from heading in a false direction. “Not knowing what to do, we start to pay real attention. Why? Because for those who are really lost, their life depends on paying real attention. If you think you know where you are, you stop looking.”

If you’ve had a tough year, please know it won’t always be like this. You have the ability to change direction. You just need to start with fully admitting where you are. And know you’re not alone.

There is no way of being fully human without at times being fully stuck, or even completely absent; we are simply not made that way. There is no possibility of pursuing work without coming to terms with all the ways it is impossible to do. Feeling far away from what we want tells us one of two things about our work: that we are at the beginning or that we have forgotten where we were going.”

How did David Whyte overcome his burnout?

He found his way home, through writing.

“It was a home I would reach, through writing my way there.”

I’ll be doing the same, starting with this review.

If you enjoyed this, stay tuned (or even better, subscribe below) for a lot more to come in 2022.

May you “treat barriers not as things to be overcome but as representations of a bigger pattern” (to quote Whyte one last time), experience flow, and achieve your wildest dreams for 2022.


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Cover image by Majestic Lukas on Unsplash.

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