Why Strategic Planning Is So Hard for Creative People

“The essence of strategy is that you must set limits on what you’re trying to accomplish.” — Michael Porter

Big-picture planning, aka strategic planning, can be really hard work, and not for the reasons you might expect.

It’s easy to think that the hard part of the planning is the conceptual part. When you do strategic planning right, though, you see that it’s actually not conceptually hard — it’s not rocket science.

No, what makes strategic planning hard for creative people is that, when you do it right, it comes with some sadness, frustration, and regret. Given the real constraints of time, energy, and attention, some projects will lose out when they’re in a project cagematch, but we’re often not ready to accept that we can’t do them.

For instance, it wouldn’t make sense for me, personally, to choose goals that require a lot of travel to accomplish. The disruption of travel prevents me from doing a lot of other things. One of the things that’s impressed me most about Chris Guillebeau is that he can be prolific and effective while traveling.

Contenders for me are my book and my dissertation. A dissertation and a book may be out of my reach, though. Odds are, neither will get done, and that’s unacceptable. Been there, done that. My closet is full of the T-shirts from that theme park.

And therein is that sadness and frustration. Both projects are meaningful to me. The level of short-term impact may be dramatically different — I could write a book that many thousands will read versus a book (dissertation) that all of 8 people might read, and 5 of them have to because they’re on my committee — but the long-term impact of my finishing my doctorate (for me, if nothing else) may be greater.

If I see that I can’t do both, then I’ll be sad and frustrated. It’s easier to not make a choice about it.

Don’t Just Put It on the List

You might be thinking, “you could always put it on your list. So what if you don’t get it done?” That sounds good, in theory.

In practice, it’s the seed for a story that I don’t see being favorable. Creative work has this simultaneously exciting and annoying fact about it: it’s never really done. Yet one of the precepts that my research, observation, and work in the trenches have yielded is that we are most satisfied when we’re making progress on the work that matters to us. We need not to finish, but to see progress.

And this is precisely what messes us up when it comes to both strategic planning and being successful in Project World. We might get emotional satisfaction from making progress on things, but our holistic success depends on our actually finishing things.

As I work with clients on strategic planning, I know we’re not done until we’ve worked through some sadness and frustration. If we haven’t let something go that matters to them, we’re not being realistic yet. Yes, I know that realistic is a term that creatives, entrepreneurs, and leaders wish would go away or consider to be scarcity thinking; it’s also true that a bit of our path depends on being functionally delusional. But one of the best disciplines to cultivate is that of focusing on the fewer things that really matter and actually getting behind them. Remember: “Not Now” doesn’t mean “No”.

It’s not that I enjoy this phase of the planning process with clients. It’s that I’ve learned that if we don’t do the planning together, it might not get done until it’s too late. The project cascade will already be in effect, and we’ll be reacting to meet or adjust commitments and expectations at the cost of actually meeting them.

So, as I work through my own strategic planning, I know that I’m making progress if I’m sad and frustrated. That’s not a sign that something’s wrong with the process (or me), but rather a sign that to be human means to be bounded by space and time.

And those few things that get chosen better damn well be worth it. Everything we do comes at the cost of something else we could’ve done.

It Might Not Work — and That’s Okay

By the way, that very sentiment — “this better be worth it” or “this must work” — also sets up a lot of story, too. How many times have you regretted choosing one path over the other, only to have that regret paralyze you when it’s time to make another choice?

Better to approach it from a “This Might Not Work” mentality, as Steven Pressfield explains one of Seth Godin’s hallmarks. Sure, what you’re planning to do might not work, AND it’s worth going after. Besides, success often comes when you’re not looking for it, anyway.

What we often fail to consider, though, is that “This Might Not Work” is also true of whatever else we might or might not have put on the list. We instead assume that what wasn’t chosen would’ve been successful. I’m not sure why we do this, but I suspect it’s because we don’t want to go through the heartache of both starting over AND potentially seeing that we chose wrong again. That, and most of us have learned to be overly critical of ourselves, to the near-exclusion of practicing self-compassion. (I have a whole closet’s worth of those T-Shirts that I’m now cutting into rags.)

I wish I could make the emotional part of strategic planning less of a challenge than it is. I hope that by being aware of it, though, you’re able to work through it better. Because, trust me, if you’re not working through it, you’re not planning to do your best work — you’re only hoping to do it.

If your big-picture planning isn’t making you emotional, you’re not done planning yet.

On the other side of that emotional work, though, is the awesome feeling of learning just how amazing you can be and seeing your best work being received by the world. You can’t be everything to everybody all at once, but you can do epic shit the same way anybody does: choose what matters, actually commit to it, and really show up.

Get to it.


Charlie Gilkey is an author, business advisor, and podcaster who teaches people how to start finishing what matters most. Click here to get more tools that’ll help you be a productive, flourishing co-creator of a better tomorrow.


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