3 mistakes I made in 2021

There are plenty of planning strategies around the new year—setting a handful of key goals, for instance, or identifying a word as your mantra for the year. Author Tim Ferriss suggests something slightly more labor intensive: a calendar review of the prior year in order to identify activities (or people) that were the source of disproportionate pain or pleasure.

It’s a good idea, but amid the eggnog and gift wrapping, who actually takes the several hours required to meticulously comb through the last year’s detritus? I did, and here are three mistakes I discovered I made, which I’ll be learning from as I set my goals for 2022.

1. Doing Things the Same Way as Everyone Else

It’s only in the past couple of decades that executive coaching has become a widely understood concept—and it’s even more recent that it’s been viewed as a tool to help successful leaders grow, rather than as “remedial help” solely for underperformers.

So it’s no wonder that many coaches have clustered around a common framework for how we deliver our services. Why make it harder on ourselves by having to explain the concept and the methodology, too? Until recently, like many coaches, I’d structure my engagements in six-month blocks, meeting every two weeks.

But in 2021, I came to realize two things: First, many clients actually need more time in between sessions in order to execute what we’ve discussed; and second, I also preferred meeting on a monthly basis, rather than biweekly, because more things had occurred that clients wanted to talk about, and therefore conversation flowed even more effectively. Moving forward, my coaching engagements will meet monthly—because I believe it’s the best for my clients and for me.

As you review your calendar for the past year, it’s useful to ask yourself two questions: Are there instances in which you’re doing things the same way as everyone else? And if so, are you making a conscious choice or just operating out of habit? Now is the time to question not just what we’re doing, but how.

2. No Margin

This past September, I launched a new book, The Long Game: How to Be a Long-Term Thinker in a Short-Term World. I wanted to give it a good promotional push, but in retrospect, I went a bit overboard. For the latter half of the year, my calendar frequently had 8, 9, or even 10 meetings per day. It’s no wonder I felt stressed: I had to strategize about the most basic of activities, like when I’d be able to take a bathroom break.

For most of us, there’ll be “clutch times” when we need to focus intently on work—book launches, or tax season for accountants, and the like. A few weeks would probably be acceptable—but it certainly shouldn’t last an entire half year.

I’ve come to realize, it’s essential to set clear boundaries because emergencies, or time-sensitive issues (like a client needing to talk to you that day), will inevitably come up. If you have 10 meetings that day, even a small disruption can throw the entire system into chaos, so it’s essential to build in margins. For 2022, I’ve committed to having a firm limit of no more than five scheduled meetings per day. I may end up taking more meetings if the need arises, but at least I’ll have the space in my calendar to allow for it.

3. Nebulous Conversations

Reviewing my year-end calendar, I identified several companies with whom I’d had protracted discussions that went nowhere. I pursued all because, had these conversations coalesced, the result could have been lucrative: a six-figure contract, or an equity stake. But the leaders didn’t seem to know what they wanted, so we swirled endlessly. Earlier in my career, it probably would have been worth my time and effort to pursue, regardless—since you never know where it’ll end up, and it could be exciting, or a learning experience.

But as you advance professionally, it’s important to recognize that you have less time to waste and you can’t afford to endlessly “see how things play out.” In the future, I’ll be more careful to guard against these amorphous chats that seem to hold promise but end up just as hazy as they began. In order to determine early on if it’s a fit, I’ll attempt to make the other party do a bit more of the upfront work of explaining precisely what they’re looking for.

There were plenty of highlights for me in 2021—whether it was something “big” and professional, like having The Long Game hit the bestseller list, or something small and personal, like monthly haircuts with my friend Ron. But as with many things, we can often learn the most from analyzing our failures, and the places where we fell short.

Making the time to comb through our calendars at the end of the year is—let’s be honest—a hassle. But a few hours’ worth of analysis can provide invaluable insight into where we experience friction—and where, through small adjustments, we can make the biggest improvements in our lives moving forward.