Lead Like You’re Retired (Part 1: Experiment)

In my last post, I talked about my dissatisfaction with the R word and some of the things I’ve learned about ‘whatever you call this thing when you don’t work one full-time job anymore’. For you, dear reader, and to cut down on my word count, I’m just going to use the R word from here on, so I can focus on some interesting things I learned in retirement that help make me a better leader and a better person. One of those things is the magic of experimenting.

I thought about retiring for ten years. While I was excited about the prospect, I was also terrified. I put a lot of pressure on myself to create the ‘perfect next life’. I felt like, for the first time, I could do anything I wanted. I just couldn’t figure out that ‘one thing’ I was meant to do, and I didn’t know how to deal with the pressure of making that decision. [Where’s Curly from City Slickers?!]

Then I read Designing Your Life by Bill Burnett and Dave Evans. The authors adapted their product design expertise to life design. One important early lesson: There isn’t just one great life out there waiting for me, there is an infinite number.

This was freeing for me because I tend to commit to something for a long time. In 33 years, I’ve worked for three companies. I’m working on the second half of my 50th wedding anniversary. Heck, I have a pair of sneakers that are older than my 26 year old.

Many of us imagine we might live the dream of making a career out of our favorite hobby. But how do we know what that is really like before we’ve committed to it?

I only know one person that built a career out of his passion and he did it twice. The second time has turned out well from a business standpoint, but it’s about killed him personally. It’s hard to know whether something you think you will love will actually work out in the long run. Ask anyone that’s dated anyone.

The key lesson from product design is to experiment. The framework for Designing Your Life starts out by clearly documenting the must-haves of your life. What are your values and non-negotiables? Paint a clear picture of where you are now and some potential avenues to where you want to be. Then experiment. Don’t fully commit to your first idea – test it.

The key for me to getting unstuck was to consider retirement as a series of experiments that all lead generally forward. I don’t have to commit everything I have on one endeavor with a lot of unknowns. Just thinking about each mini-career as an experiment has been incredibly freeing.

We did a lot of experiments when I was in Engineering school. One of my favorites was when they made us pay to go to summer school so we could be locked in a room with three random teammates and equipment that didn’t work when it was manufactured in the 1940’s. We couldn’t come out until we had results, and if a random group of poorly paid graduate students didn’t like what we had to say, we got to work on the weekend too. Come to think of it, that really prepared me for the working world.

In my first real paid job, all I did was experiment. It was like a geeky, totally unwatchable version of Top Chefs. I worked in a ‘kitchen’ with a seemingly endless supply of ingredients that I tried to put together into products that were better than our competition’s. The mixer was about the size of a dump truck and it seemed like I only got to use it at 2am on a Saturday.

That experimentation had a clear goal. We knew the properties we needed, who would buy gobs of the stuff and what they would pay for it. We didn’t know exactly how to get there, so we tried mixing up some stuff, tested it, and went from there. We had a deadline and clear metrics. We were held accountable. But we didn’t know what to put in the mix, how long to bake it or at what temperature.

After that job, it felt like experimenting stopped. Business didn’t feel like a place that was comfortable with experimentation. If you were experimenting, it meant you didn’t know what you were doing. It certainly felt that way to me in big corporate life. Here’s what you need to do, when you need to do it, and, more importantly, how you’re going to do it.

Even as the leader of a small company, I didn’t talk about experimenting very much. Our leadership team went off every so often and came up with a strategic plan to tell everyone about where we were going and how we were going to get there. Somehow, the strategic priorities got set aside to do the stuff that had to happen every day. You didn’t have time to experiment with better ways to do your day job. You took the process handed down to you, no matter how crazy it sounded, and you turned the crank over and over.

Experimenting sounds like fun. Much of the work we end up doing in the office is the opposite of fun.

Every strategic plan we ever did probably should have been labeled ‘experiment in process’. But we always acted like we knew it was going to work. Maybe we were afraid that people wouldn’t put everything into a new initiative if we didn’t act that way. But I wonder what would have happened if we admitted that it was an experiment that we will systematically test and adjust if we don’t see the results heading in the right direction.

Sure, there are times when you have to ‘burn the ships’, like Hernan Cortes did when he arrived in the New World. But that was when there was a stark choice – fight or die. There was no experimentation involved and only one result mattered at the time to Cortes. No wiggle room, no dissention, no questioning. How many initiatives are really that limited?

Some of the best things we did were openly labeled as experiments. When we realized that we, like virtually every other organization, did not know how to effectively compensate people, we had some great discussions about why that is so difficult to do well. We acknowledged that we don’t know what good looks like because we’ve never seen it. We took a step that seemed logical and went from there. We’re better than we were.

The other day I was talking to a friend who is approaching retirement. He loves his work and he’s got a wealth of experience, but he’s never been a consultant. He is unsure about what that would feel like and how it could fit into his next great life. I encouraged him to run an experiment. I might have imagined it, but I could see his shoulders relax a bit just thinking about that. Sure enough, not long after, he went to visit his first prospective client, knowing that it wasn’t the most important meeting of his new life because the goal was learning and not winning the job.

That same week, I was talking to the founder of a growing business who was worried about the path ahead and how to ensure that her business would go on when she retired. We brainstormed a lot of ideas about the next great life for her business and she was nervously wrestling with each option. When we suggested that she experiment with some of these, the temperature in the room dropped and she took a big deep breath. ‘Yeah, I like that. We experiment all the time here with our work, so why not experiment our way into the future?’

The word alone relaxes everyone. It drops the pressure and allows us to think more creatively. It keeps us from becoming so locked into something that we cannot back out of it gracefully, even when it clearly isn’t working. We acknowledge that we don’t know what will happen with our wonderful plan. When you mix in people and life, how could we know?

I wonder what would have happened if I had used experimentation more as a leader. So far, it’s been an important part of my retirement design and it’s made me a better leader and counselor. I’m less convinced that I absolutely know the way forward. I listen more to opposing views and I’m more curious about other perspectives.

Thinking about life as one long series of experiments stresses me out less. Or maybe it’s just that I’m in retirement 😊.