Five Learning Moments After a Year Working For Myself

Today in Ottawa I delivered my 33rd and final keynote of 2019. What a thrill it has been to share my thoughts on leadership, purpose, open thinking and employee engagement to roughly 15,000 people across five different countries this year. It took over 150,000 miles of airline travel to do it and a lot of espresso and melatonin. (No, not together.)

Also, Air Canada really, really likes me.

It was a year ago that I announced my departure from TELUS, an organization where I had spent the previous ten years as a full-time team member doing fun, culture-changing things.

To be honest, I wasn’t really all that prepared to go solo. I had been mulling it over for a few years, but given I had never worked for myself before, there was a lot of learning to do.

In the spirit of it being the season of giving, I present to you my five learning moments after a year working for myself.

#1 If You Build It, They May Not Necessarily Come

Prior to going out on my own, I published three books, wrote over 500 articles for Forbes, HBR, HuffPost and my own site, as well as participating in multiple podcasts and webcasts. Just because I was “out there” and thought I had already built a pretty decent public persona and social media following did not magically mean people instantly wanted to hire me. By the end of 2019, I decided to hire a marketing/branding company to figure out a much better business development and branding plan for 2020 and beyond.

Lesson Learned: Don’t rest on your laurels. My network is my net worth. (But tend to it like a garden that needs water and weeding.)

#2 It’s Hard To Detach From the Thought of Money

Since my first “real” job in 1994, there has always been an organization kind enough to send me a bi-weekly paycheque. That ended on December 31, 2018. For 24 years I never had to worry about the next round of cash invisibly flowing into my bank account. The moolah just showed up. Thus, I never really had to worry about money. (I had to worry about spending it, and saving it, but not earning it.) When that changed on January 1, 2019, I found myself constantly thinking about money. Where would it come from? Would it ever arrive? Did people lose my email address? Is it because I’m bald? I soon realized you can think too much about money, and it might ruin your confidence if you’re not careful.

Lesson Learned: Trust the process, and believe in yourself. The money will appear if you’re good at what you do, so stop overthinking everything that has to do with your revenues.

#3 I Can’t Believe What It Takes to Start a Business

I knew there were administrative tasks that had to be carried out to start up and run a business, but I wasn’t prepared for the volume. Insurance, more insurance, expenses, accountants, bookkeepers, lawyers, expenses, more expenses, licenses, payments, follow-ups, suppliers, partners, government, even more expenses; the list seemed to go on and on.

Lesson Learned: There is a first-year “administrivia” learning curve. And, take steps to outsource whatever you can.

#4 Saying Yes To Everything is a Bad Strategy

For the first time in many years, I had no direct reports and no team to lead. My thinking was that I’d have loads of time to backfill. Without doing any sort of bandwidth forecasting, I said “yes” to way too much. The first few months of 2019 were fine but when the calendar turned to September, I only then realized my mistake. Worried that I wouldn’t be making any money (see #2 above) and that no one would ever contact me again (see #1 above) I said yes to just about anything and everything requested that was to occur in September through December. The result? An insane schedule with too much travel and too many encroachments on my calendar.

Lesson Learned: Allocate time in your calendar for business development & planning, thinking and doing. Accept work that fits your limits. Don’t compromise.

#5 It’s Okay Not to Be Busy

For 24 years there was a cadence, a workday familiarity. No matter what role or organization, I knew what I was supposed to be doing, when, where, and with whom. Shifting to full-time solopreneurship caused me some nervousness. Prior to the busy fall season, I wasn’t always certain where to be, what to do, or how to do it. At times I was lost, concerned that some mysterious figure was going to pop out and chastise me for not being busy enough.

Lesson Learned: Decompressing from 20+ years of senior leadership roles with multiple priorities takes time. Being a solopreneur can leave gaps in your schedule, so use your time wisely to learn, write, think, plan, exercise and stare out the window. (It’s cathartic.)

Have a fantastic holiday season. I hope to see you in 2020.

PS. I’ve finished the draft of my next book. Look for it in 2020.

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One comment on “Five Learning Moments After a Year Working For Myself”

Hey! I'd love to read what you think. Surely you have an opinion. Love, Dan.