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 hardit’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.

I was thinking about this this morning as I was considering my strategic projects for next year. Last week, I officially came out of my unofficial leave of absence in my doctoral program. I plan on finishing that up next year.

That’s one Big Project down. I get no more than 2 more, and that project favors or disfavors other Big Projects. (Big Projects = objectives or initiatives for our planners, in case you use those to help with your planning.)

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.

A contender for 2014 is Start Finishing (my book on finishing the stuff that matters). 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. (Click here to share this on Twitter. Thank you!)

On the other side of that emotional work, though, is the amazing 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.

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      • says

        Ahah, Charlie!

        My artist’s-brain just spotted the reason it’s so “much easier … to see green grass on the other side of the fence”:
        When you’re looking at *your own grass*, you’re looking down at it, at the spaces between the blades.
        When you look at the other-guy’s, you’re looking across the top of it. You don’t see the bare spots or the – difference between grass and weeds – it’s all green.
        It’s parallel to “Comparing my Insides to your Outsides”…

  1. says

    I always appreciate the way you express thoughts Charlie.
    I could listen and learn loads more as you talk about planning and making progress.

    “So, as I work through my own 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.”

    Those words of yours are some I relate to, in that to be ‘bound’ as a creative often feels like I’m not living.
    My goal is to learn the fine art of balancing progress and loving life in the same breath – then to pepper in some purely creative [don’t give a shit] rewards.

    • says

      Thanks, Siita, and I so get where you’re coming from re: being bound.

      And here’s the irony: without time constraints, most of us flail when it comes to creative work. So it may turn out that being bound by space and time is our creative saving grace, as it were. This seems to have been Tolkien’s view, as his greatest work – the Silmarillion – has as Man’s grace the fact that they die, whereas the curse of the Elves is that they did not.

      Something to consider, no? :)

  2. says

    Do the book. It’s a crucial subject and Start Finishing is such a great title. I’m looking forward to it.
    (Not waiting for it before taking action, just looking forward to reading it.)

  3. says

    “Everything we do comes at the cost of something else we could’ve done.”
    Working through this is the toughest part. There are so many possibilities and interesting and wonderful ideas and projects to pursue that deciding what not to do is just as important as picking the right projects to put your heart into.

    • says

      For real. It goes further: the more successful we get, the more we have to decide what not to do simply because more opportunities find us. The rich (in opportunity) get richer, at the same time that they don’t get more time.

      A post I’ve been sitting on for a long time is about the strategic value of simple yes/no questions. Few things are more helpful as a decision framework that almost automatically answers the question. In fact, that’s pretty much what strategy is.

      • says

        I love your definition of a successful strategy framework; one that helps you answer yes or no.
        I worked in a floundering organization because no real strategic framework existed and the default “strategic” answer became yes, to everything. And people thought this was great.
        Sometimes (but not for all) a young organization’s strategic advantage can be the ability to quickly say yes. This can also be a large resource-rich organization’s advantage. But for so many in the middle, focus through strategic yeses and no’s becomes vital to long term viability.

  4. says

    This is so relevant to my work at the moment! I was planning my biz goals for 2014. The list was long and wishful, and many things were crossed out until it was as focused and strategic as I wanted it to be. (Went from almost 20 major projects to 4. One each quarter, with relevant content strategy. I can do that.) Having a solid plan for the next year is satisfying, but bittersweet. Knowing what I will be doing means I know what I WON’T be doing, either – no matter how fun or nice those things would be.

    And it is SO easy to regret the time you spent on failed or mediocre projects. (What else could that time have gone to, you know?) Best to learn from mistakes, remember everyone’s human, and get back on track to mastering your work.

    It’s all about the intrinsic value, right? (Sorry; finally got my hands on a copy of Dan Pink’s book ‘Drive’ and read it in one sitting today. Couldn’t put it down!)

  5. says

    Charlie, thanks for sharing your thoughts on this. I couldn’t agree more. I’ve been thinking about this a lot lately. I realized that there’s just no way I can work full time, upgrade my skills, get a master’s degree, and start a side business. Even three out of four is asking for underperformance and resultant failure.

    So it’s exactly as you so eloquently said. I’m doing the emotional work of saying no. As much as I hate giving anything up, I’ve decided that I have to defer the degree and side businesses for next year.

    Saying no to long held dreams and ambitions is HARD! I’ll do my best to remember that everything I choose better damn well be worth it.

  6. says

    I can’t tell you how often I remember you saying “not now doesn’t mean never”. And the big picture planning creating emotion is going to stick too. Thank you Charlie.

  7. Amiel says

    Good stuff here. I’d vote for the dissertation by 9/1, then set epic goal of book first draft by next thanksgiving. As for strategy, my take is that when we take a broader view of what strategy is and how it forms, creatives see their contribution more clearly. Have you read Minztberg, eg Strategy Safari? He puts Porter in his place– not down but as just one of rights schools of strategy. The key notion is emergent strategy–it changes everything.

  8. says

    Great article Charlie.
    So true that there is sadness in letting go of the “not now” ideas – as there is regret when the ones you do choose don’t come to the fruition that you hoped they would … despite your focus, hard work and commitment to them. That also happens, and it IS progress, but not as satisfying, as you say: “We might get emotional satisfaction from making progress on things, but our holistic success depends on us actually finishing things.”
    I think in the planning and choosing-what-to-focus-on process it is important to keep a “not now” idea list. To know you have that incubating and can get back to it (while freeing up your gray matter to focus on the “chosen ones.”) These ideas are important to creatives (and entrepreneurs are all creative/idea people), and it’s important to know they haven’t been abandoned and won’t get lost.
    Also, what’s really important to creative people is actually creating something. Seeing it come to life. So once chosen it is worth getting all the help possible to make sure that happens.
    “Actually finishing” IS the creation. Then you can move on to creating something else.
    Cheers, Dolly

  9. says

    nice post charlie! i enjoy reading your post and i totally agree with you that its really hard for creative people to be strategic because all they need is just one moment and boom they know what to do. :)

  10. says

    So much to (painfully) process here, Charlie.
    “Hoping” instead of “Actually Planning” and then “Taking Action on the Plan” – I’ve been doing that most of my life.
    And, seeing *progressing but not completed* as the best state I can achieve – that too. Ouch!

    Thanks (I guess) for the kick in the butt…

    Bright Blessings ~

  11. Great post says

    I love this post. Someone posted the link on Facebook and I read the title and came here in order to read the whole text because it trully is what I need to read tonight.

    There was a young man in Russia. He was extremely talented in painting. He loved painting. But he gave up being a painter because he thought that being a doctor instead of a painter is by far more useful to the people around him. So, he studied medicine in the University instead of studing in the School of Arts. Later on, he became a very famous doctor and saved a lot of lives.

  12. says

    Strategic planning (for myself) is by far my biggest weakness, Charlie. I take one day at at time to preserve a sense of calm in my life–to tame the variables–but I know I’m sacrificing long-term peace of mind, and the accomplishment of some of my goals–some I may not even be aware I have yet. I’m so looking forward to working on this with your guidance in the coming months!

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