A Case for Short Term Goals and Un-Planning

Today’s December 2nd, which means today marks exactly three months since I put my business on hold, and set off on the Appalachian Trail.

My, how things have changed.

In August, I lived in my parents’ basement in Connecticut. Today, I live in a finished attic on a rural English estate with a walled garden and an indoor pool (and in a week I’ll live somewhere else entirely). Could I have seen any of this coming? Could I have planned it?

In his interview with Derek Halpern, three-time best-selling author Tim Ferriss says that the key to his shocking success hasn’t been strategic planning, as many might first think. Instead, he lives by a series of three to six month goals and micro experiments. There are at least two major benefits for doing this.

First, he says, it lets him treat the projects in his life as tests, rather than major life decisions. If you launch a podcast, or open an online store by saying to yourself Okay, this is what I’m doing for the rest of my career then you face a tremendous downside if it doesn’t work out. You’ve failed.

The mere threat of failure is what keeps many people from trying things, and so this idea of committing to some long-term goal or plan can sometimes keep you from ever getting started.

By contrast, if you view something as a test, then there can be no failure; There’s only feedback. If it tanks, you take a look at what happened, and incorporate that new knowledge into your next project. You’re not a failure, you’re just learning. That feels a lot less scary.

Second, when you avoid long-term planning it leaves you open to opportunities you didn’t know were waiting. To create long, multi-year plans is to ignore the fact that the future is actually unwritten. It’s to risk being over-committed to a plan that’s not working, or one that only realizes part of your potential.

When Derek Sivers started his company CD Baby, his boldest vision predicted 1,000 clients and three employees crammed into his living room. Reality had more in store.  When he sold the company for $22M, CD Baby had over 200,000 clients, eighty-five employees, more than twenty-thousand square feet of warehouse, and millions of transactions a year.

Staying agile allows you to take hold of opportunities that are even better than you imagined possible.

All of this has been rattling around in my mind today, as I look back on what the last three months have brought. It’s rung especially true as I look forward to the next year, and the resolutions that would typically accompany the changing of the calendar.

This year there will be no resolutions. No goal by which I judge the success or failure of 2016. No grand vision for my life or work.

Just a handful of three to six month experiments that I’m really excited about, and hopefully the courage not to take them too seriously.