What’s the Plan?: The Power of Experimental Thinking

I’ve always been a planner. When I decided to close my business, it seemed irresponsible to do that without having a plan for what was next. The “new” business plan sounded essentially like what I’d been doing for the previous decade but on a smaller scale.

Over the next two years I wrote FOUR versions of a new website. They all sounded like variations of the business I was closing. I knew that I had no idea what I was doing, yet I kept making plans. Having A Plan was comforting even though I felt frustrated and constricted.

Eventually, I stopped making plans and decided to take a month off instead. One month became eight months – the best, most insightful and productive of my life.

Anytime we contemplate change, other people want to know what our plan is. Many will make us feel like a lunatic for having no plan, especially the people who love us most, because they worry about us. Even once I knew what I was going to do, it wasn’t enough to satisfy some people. “How are you going to make money doing that?” they fretted. “Who’s going to want that service?” they worried.

Not only do we want to know what the plan is, we aren’t satisfied unless the plan sounds like other plans. I’ve developed a new perspective on plans.

Plans have their place, but it is not to help us figure things out. A plan is useful only after you know what you’re doing.

To figure out what you’re doing, you need experimentation and play, which is essentially what I did with my “time off”. I wandered in directions just because they seemed interesting – improvisation, choreography, a writing retreat, mindfulness, travel. I reintroduced creativity into my life as a priority. I started to accept myself and everything about life as a work in progress.

Looking back, I can see that my misguided, discarded plans were useful in showing me what didn’t feel right. Thankfully, I didn’t forge too far ahead with them as I would have in the past. I just wish that I’d THOUGHT of them as scenarios and experiments rather than plans – it would have been more fun and less stressful. I’d have discarded them sooner and moved on more quickly.

The right path became visible only after I stopped looking for familiar ones. Having NO PLAN finally led to knowing what to do next, and now the plans are flowing from that – I’m not forcing them. They’re kind of writing themselves.

Run some experiments

If you’re contemplating change, treat your options as experiments and scenarios. “What if” everything. Refrain from writing plans; when the right direction presents itself, the plans will want to write themselves.

To help the process, try the Work In Progress and/or the Word Salad activities that you’ll find at the end of those previous blogs.


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