A second chance at CEO
After I wrote my last post about becoming a Boomerang CEO and how I’d be doing things differently this time around, I immediately trampled all over my own boundaries, worked all weekend, and arrived at a prescheduled surgery yesterday completely depleted. The moment they gave me an IV, I passed out in the chair.
In my last post, I wrote about my intentions to maintain the balance I’ve found in my life running my own founder coaching business. I pledged all the things I’d do differently, with the perspective of a two-year break from being a founder, the lessons learned from a spiritual journey that took me to the edge of the planet and back, and the observations from coaching over 40 other founders.
But taking over the reigns on a bucking startup is hard. It reminded me how much of what we do as founders is hard. Even though I now know what my sustainable work hours look like, the sheer overwhelm of trying to get a handle on things drove me to compensate for chaos by adding in more hours. I know it can’t work that way long-term.
Even though I know what to do - where to focus my time, how to spend my energy, and what capacity I realistically have to work on this business - I didn’t do it starting day 1. I’m telling myself some sort of story that I’ll get to the work-life balance thing once I get a handle on what’s going on right now. There are urgent things I am days behind on with the unexpected transition, and the story I chose to believe is that I have to do all those things yesterday. (I couldn’t do them yesterday because yesterday I was in the operating room - and yet the world did not fall apart.) My story is sustainability will come after I do those things.
And yet the way we live our lives today is the way we live our lives.
The way we intend to live our lives tomorrow is not the way we are currently living our lives.
Almost all of the founders I’ve coached have faced some form of this narrative: I’ll do XYZ (which is the most important thing for me to do) when I get enough time, after this next milestone happens, once I hire this key employee, after Saint Patrick’s day… The reasons are infinite. But once again, the way we live our lives today is the way we live our lives.
If we (founders) aren’t prioritizing the most important thing with the greatest importance, then we’re prioritizing the wrong thing. And that’s hard because there’s always a million urgent but less important things.
What happens to our companies when we do this? We send the message to our teams that the most important thing is not, in fact, the most important, otherwise we’d be spending our time there. And our employees learn from our example that it doesn’t matter if they are working on the most important thing. When we prioritize what’s urgent over what’s important, we tell our employees (whether directly or subconsciously) to do the same.
And then what happens to our business? We sprint hard all the time to accomplish a million micro-tasks but no one is steering the ship with intention.
Why do we do this? As I’ve gotten into the nuance of this with founders I’ve coached, this is a recurrent theme. There’s a dopamine reward system that hits every time we accomplish a small task - unblock an employee by responding to a Slack message, check off a minor item on our to-do list, etc. It feels like progress to do many micro-tasks in a day, even if that means we delay the more important ones indefinitely. The work that seems to get punted is the high-level strategy, the planning for what we’ll do this quarter, the team changes that need to be made, the bigger product pivots, etc. I’m guilty here too.
The way out of this is to choose to do it differently and to hold yourself accountable. As a coach, this is perhaps the greatest gift I give to founders. I’m simply the person who asks you each session what the most important thing is for your business and helps you get that done.
Whether that’s blocking time on your calendar, pairing with a teammate, exploring the fears that are blocking you, or simply holding you accountable to the goals you state out loud each session, we find the thing that works for you and we do that.
And now I have to find the thing that works for me…