Space, experience, trust: Thoughts on life without a plan

For the first time, I feel change and connections happening organically. I’m meeting people and talking about new ideas at a clip that I can almost feel but that I did not “push”.

The challenge with connections and ideas bubbling up like this is that too often, you notice it happening only through a passing glance or in complete retrospect, sometimes when it’s too late to take full advantage of an opportunity, or sometimes when it’s too early and you’re not ready to trust the potential.

In the past, this hasn’t set well with someone like me, who believes challenges should be anticipated, opportunities are everywhere, and personal expectations have to be high to be prepared. I’ve believed that a good plan is the only bridge from where I am now to those opportunities.

This was obvious in how I planned for this year. I said I wanted to have a more creative year. I shaped that goal into a stringent plan, believing the disconnect between my life and its creativity was a matter of structure. What I’ve learned is that my creativity was actually lacking space.

This year feels like it could be one of my most creative yet, despite having abandoned the rigorous system I established for myself, as well as my structured definition of creativity. I wanted to finish a book, write a lot of poetry, and be a creative writer. Instead, I’ve met a lot of new people, identified a lot of new opportunities, and discovered new questions to ask about myself and my community.

I didn’t wake up one morning and decide this would happen. I don’t know what clicked along the way that left me with this approach, but I can point to a few factors that must have been influential:

Space. Without a doubt, working on a mix of projects between my family businesses, consulting, and community groups has allowed me to explore opportunities freely. Time is my own currency now… my success is judged based on the results of my efforts rather than the number of hours invested (and when and where they were invested).

Experience. I’m starting to sense the difference experience makes, and now I want to reframe that word. The mistake we’ve made as it relates to experience is equating it to qualification. The power of my life and professional experiences is not that they make me more or less qualified… instead, they make me more steady and empathetic, help me gain exposure more easily to new people and networks, and in turn reduce some of the risk of living without a tight plan.

Trust. Planning is a great way to cover deficiencies in experience. You might plan more the first time you visit a city than the second time. This urgency to plan and anticipate is connected in some way to matters of trust. I didn’t trust my college advisor and her thoughts on my college journey, so I created a plan that showed her it’s possible to graduate in three years. Ok, impressive maybe. But it reinforced an unhealthy expectation/assumption: if you have a great plan, you’ll get to a great spot, and you’ll get there more efficiently than the next guy. Or, put another way, trust the plan more than the desired outcome.

This isn’t about regret, but it is about reflection. Regret undermines experience, which in turn would change where I am now. And I like where I’m at. Appreciating that one way of living (and planning) got me here helps me realize I’m in the midst of recreating that (or letting it recreate itself, I guess) to see where I land next.

As I’ve thought about this, I’ve mentioned it to some of my favorite older, wiser people locally. One person who essentially makes plans for a living told me she’s never had one for her life… I was probably unreasonably surprised by this. I’m really curious now about other people’s stories and their own process for planning or not planning, identifying new opportunities, etc. Especially as we lose some of the traditional structures for getting from point A to point B, will flexibility and space become the values, rather than structures, formulas, and plans?