Lack of Strategy as a Core Value

Or maybe it’s just insecurity? In any case, here are 3 short stories.

In Monday’s post I said that everyone is making it up as they go. What has that looked like for me? Here are 3 short stories.

1. “It was a great event, I just didn’t hear a single speaker...”

The other day I mentioned WDS, the big event I used to host each summer. One of my roles was to emcee the main stage programming, which included everything from keynote speakers to attendee stories to some unexpected surprises (one year we made it snow in July, another year we parachuted snacks down from the rafters, etc.). 

But back to the keynote speakers. Over the course of 10 years we had more than 100 of them, including many A-list, household name luminaries. 

During and after the event, attendees would sometimes ask “What did I think of so-and-sos talk?” Well, here’s the thing: I almost never heard the talks! 

Even when I was sitting to the side on stage right, or in a small green room a few steps away with a remote video feed, I rarely paid active attention. I was too busy thinking about what came next or worrying about some other detail.

After a speaker finished, I’d go back out on stage and say something like “Wasn’t that a great talk!” ... which wasn’t necessarily a lie, since you can pick up on the vibe from the audience. Still, much of the time spent backstage was spent doing anything other than appreciating what was happening at the time.

To sum up: for multiple years, I did not hear most of the main-stage talks at my own conference. 

2. “Thanks for buying the course, I guess I should figure out how to make it now...”

In my early days of blogging, I had the idea to create an information product called the Empire Building Kit. I had a nice pitch and tagline for it: Build a business in a year by doing one thing every day.

I originally envisioned a 365-step outline for this course—because, you know, the whole year-long thing. But when I started writing the outline, I got stuck! I got to step 14 or something and realized, I’m not sure what comes next.

I could think of a few things, but I had no idea how to get to 365.

So I pivoted. Instead of releasing the course with an outline, I sold it as a 365-day email series, where buyers would get one step a day sent to their inbox, every day for a full year. 

Problem solved—except, of course, now I had to write the entire series. 

Which I did. For the next 9 months, writing the 365-day email sequence took up a big part of my day, almost every day. I tried to work ahead as much as possible (that’s why I finished in 9 months instead of a year), but still, I was absolutely, definitely making it up as I went along. 

It’s kind of funny to think about it now, because at the time some people were impressed with the “strategy” behind the course launch. I promise, there was no strategy! I made the decision to switch to an email series a few days before launch, and then I spent the better part of a year doing the work. 

3. “I’m going to every country in the world … in a most unorganized and inefficient fashion.”

I got my start in the blogging world by writing about going to every country in the world. The whole process took 11 years, though the first half was just my own private goal, not something I shared anywhere. But on my 30^th birthday, I made it public, and announced that I’d visit the remaining ~120 countries (out of a total of 193) by my 35^th birthday.¹ 

Which I did! But parts of it were very chaotic. 

I traveled because I liked to travel—you don’t need another reason—but that also meant I went back to the same places over and over again (typically as transit countries and cities). I also made a ton of mistakes along the way, including many that were entirely preventable.

A very long time ago in Bangkok. 📷 by Stephanie D. Zito

I got stuck in different places. I failed to get the visas I needed for several countries, so I went anyway and hoped for the best.

The point: someone who was much more organized than me could have done it way faster and far more efficiently. 

And yes, that’s part of adventure—it doesn’t necessarily need to be organized or perfectly smooth. But some of the stress was self-applied, and having more of a plan would have been … helpful? 

Looking back, do I wish I’d done these things differently? (Not really.)

The thing is, I’m still proud of all three of these experiences. I made peace with the fact that I’m not a great planner, and I struggle with being present, and that I am far from a strategist of any sort. I just do things I’m excited about! 

So that’s me. But just like going to Pakistan without a visa (for example), I do recognize that there’s probably a better way. I just haven’t figured it out yet, and most things have worked out fine, so I just keep moving forward. 

What are some ways that YOU make it up as you go?

P.S. For all parents and teachers: My friend Seth Perler is hosting a virtual summit on Executive Functions, a topic that many readers have found helpful in recent posts. Seth does great work and it’s free to attend. Sign up! 🎉

1. That’s why my Instagram handle is @193countries. Fun fact: when I started the quest, there were only 192! South Sudan was admitted as a U.N. member state in 2011, so I added it to my list and went there a year later.