The Trouble with Willpower
Needing a different skill in the face of a NO.
There’s a not-so-secret fantasy I’ve heard a lot of entrepreneurs voice over the years: the wish that some sort of catastrophe lands you in the hospital for a while, tended by a fleet of nurses. It’s a rather dark and horrible vision, the idea that you need some sort of deus ex machina to save you from yourself/your business.
Two separate newsletters referenced this fantasy in my inbox last week, and it helped me connect some dots around an idea that’s surfaced amongst my summer failure rabbit hole: the role of willpower in an entrepreneurial journey.
There are for sure certain qualities and skills that can serve as necessary boons to the hard work of building a business: a penchant for unreasonable optimism. Being able to intuit a corner and an opening when everyone else sees a wall. The ability to summon deep resolve in the face of many signals that you should just give up already.
Which brings me to willpower.
There’s willpower in the sense of not eating the cookie on the plate in front of you (aka self-control), but here I mean willpower in the conjuring sense. To summon something tangible from a lofty vision through the force of will. To launch something into the world against odds or common wisdom or sense.
Will, in this sense, traces it’s etymological roots back to desire. Wish fulfillment.
And certainly, to fulfill a wish or a desire requires action.
Would you agree that you’ve needed willpower in your own journey?
Can you think of a time that you’ve needed to take a deep breath and muscle through? Me too.
I spoke to a friend while writing this who sold her business about a year ago1, and I asked about her experience of willpower in her own business. She said she always imagined it as her “Care Bear Stare”— a light beam coming from inside her body, shooting out and compelling her forward. She remembered people saying variations of “I could never do what you do” to her over the years, which she took to mean that they might have vision, but not the willpower to do what she did (cue rueful laugh).
The thing is, as she told me, that light beam is a limited resource, it’s not sustainable to continuously blast all that light from your belly (or…whatever). Care Bears weren’t my thing as a kid, so I am absolutely not an authority on this matter, but I am pretty sure the bears had to recharge.
And so what I’ve been particularly wondering about is “when willpower is the wrong skill for the circumstance2.”
In my interview with Heather, she told me that she found herself willing someone, anyone to tell her to stop. She’d voice her doubts or signs of doom and her closest advisors would respond with all sorts bolstering messages of support and encouragement.
“Nobody was going to tell me I couldn’t do it or should stop.”
If you listen to our conversation, you’ll understand that Heather is a person with willpower in spades. And so, if I had to guess, her advisors were mirroring the force of will they were used to seeing. The person who had time and time again dug deep and muscled on when she heard a no.
So how do we discern when willpower becomes a liability?
A term to aide us: Willfulness.
Willfulness is when you impose your will on reality, which is fine in some cases but harmful when reality simply cannot be what you want. We’re given many stories from the time we’re young about the value of willpower and pushing through obstacles, but we’re not given stories about what happens when we hit concrete walls, when we do not get what we want no matter how loud we cry, and when willpower is the wrong skill for the circumstance. We aren’t really set up to fail well. Rather, we’re indoctrinated with the value of persevering and refusing to take no for an answer. But life is both yeses and nos. We don’t get what we want all the time. It sounds so juvenile and so obvious, and yet so many of us really struggle with accepting that.
— Jessica Dore, Tarot for Change, The Chariot3 [emphasis mine]
When I read Ronan Farrow’s (terrifying) Elon Musk profile, it struck me as a perfect example of willfulness in all its toxicity. In this Musk’s not unique: all champions of “move fast and break things” are tipping into willfulness too.
I’ve started to think about the hospitalization fantasy as a symptom of willpower shifting into willfulness. Because the mindfuckery of it all is that, at a certain point, it almost takes more willpower to stop the train than to keep putting one cement-encased foot in front of the other.
When I poked around for the definitions and etymology of the term Willpower, they all mostly land on control. Ah! Remember how I said that the opposite of failure isn’t success, it’s control?
So I wonder at willpower/willfulness as a space of tension, especially for those of us visionary trailblazers, where we must certainly ignore many stop signs along the way. We need willpower to create something out of the raw material of our imagination and vision. We must summon conviction and commitment, maybe a certain amount of headstrength, to put ourselves on this path.
But one of the things we usually mean when we talk about headstrong people is that they don’t really listen4.
Willfulness can create all sorts of personal suffering because, at the end of the day, we don’t have control over all sorts of things, and certainly not over other people. Some walls are meant to be broken down or scaled, but others are clear signals to attempt a different tact.
What sorts of signals are we ignoring when we hit those concrete walls? What other skills might we draw upon?
Which brings me to a third term, and a possible antidote: Willingness.
Willingness implies receptivity. An enthusiasm for showing up, meeting the moment, whatever it may bring. The difference, again, is one of control. Willpower involves force, exertion. Willingness, as Dore writes elsewhere, “active acquiescence.”
Unwillingness to give up on a vision or a dream (or, more concretely, a business) implies denial. Resistance to the idea of failure or the acceptance of a no. Willingness on the other handle invites receptivity to No as a plausible outcome, not just a sign to continue muscling.
In other words, Willingness is a skill of taking seriously all feedback, even the no’s we may not wish to hear.
When does that helpful skill of willpower tip into denial and an unwillingness to listen to guides/signs?
I don’t quite have a clear answer, except I know that it takes skill and practice to discern and witness the various types of feedback you’ll receive. Status Quo signals are different from Market signals are different from your body’s signals.
There are many no’s that you will need to ignore to bring your beautiful thing into the world and, yes, to keep going in the face of adversity. And sometimes the signals are just saying “give it a rest with the light beam for a minute, yeah?”
The source of the no or the “slow down” sign matters.
For what it’s worth, most of the trouble I see involves ignoring signals from inside the house/our bodies.
This business wasn’t in any sort of trouble really, but my friend never really liked running it. She never reconciled her radical politics and values with “selling stuff.” I asked her about sticking it out for so long and she told me: “It’s like kids…you think a thing is going to work out a certain way…but the only way to find out whether that’s true or not is to do it. [The business] was everything I thought it could be, and I didn’t want it.”
Without going too deep, The Chariot is a card in the Major Arcana of the Tarot and is often interpreted as a card about Willpower. Chariots show up all over the place as mythological symbols of course: the Bagavada Gita being an extended conversation between Arjuna and his charioteer, Krishna, while sitting around Arjuna’s chariot.
It’s worth naming the twin demons of privilege and entitlement too. I’ve noticed when I’m muscling to get what I want sometimes there’s an insidious belief that it’s my right to have it lurking under the surface... Entitlements are almost always beliefs worth undoing. There are certain people who have not had to hear no very much in their lives, and that is a dangerous thing.