How We Build The Case Against Our Own Ambitions
Pursuing our dream requires us to do some cross examining to help defeat the airtight cases we build against them.
Here’s a tale of two conversations from this week.
The client.
I had a client write out all the qualities of her dream job.
It came with an excellent list of must-haves: killer team, juicy challenges, cool mission, good boss. The things she loves to do — parachute in and fix a project that stumbled, manage big stakes, solve complex problems. Collaborate with smart people. Each one carefully couched within what she considers her lane.
The very last item, right under “I’d like to work flexibly”:
“I want to create a retreat center with a therapist friend where we can offer workshops on career development, self-care and actualization with mid-career women. This will take place in a tranquil Northern California location. I will facilitate these workshops. We will create corporate-specific retreats for tech companies like Google and will use the revenue generated from these budgets to offer affordable opportunities for people from all walks of life.”
One of these things is not like the other.
Our collaboration dashboard is full of recruiter calls for exec positions at tech companies. Meanwhile, there’s a fully formed business plan casually lurking at the bottom of the list.
The friend.
A friend I’ve known for 20 years, whose career is a thing of legends, called to talk about a position she’s interviewing for. “Interviewing” might be a misnomer, considering the dance they do when big public companies headhunt a key exec. Orchestrating, maybe? A litany of meetings and tests and conversations, an invisible network of calls and backchannel reputation checks, CEO to CEO. They probe and prod and look for weakness. A process requiring a candidate with a constitution of steel.
She knows she wants to leave her current position. She has options at a level of responsibility and compensation most of us will never see. Deservedly so. A generational talent.
During our conversation, she talked about the responsibilities and expectations of the position, and then she paused. “I have a vision for what I see as the future of my industry and practice. I see the impact that AI and other forces are having. I want to help usher in the next generation of folks as we shape what the future of this looks like, together. I’m hoping I can use their resources to do that.”
I said, “Why don’t you just do it on your own? It’s such a clear vision, you could absolutely build that.”
She gave me an immediate and decisive: “I can’t. I’m not ready.”
Why not?
Her kids are about to go to college. She wants the bandwidth for them and for her family in the coming year. She wants to deepen the relationship with her partner and support him as their parents age.
“Do you think the job you’re looking at — at the compensation they’ll pay you — is going to take less bandwidth from you than doing your own thing?” I don’t know for certain. But I cannot imagine a world where that would be true.
The case.
When you’re deferring your dream, you’re often working very hard. It’s not out of a lack of motivation or fear of hard work. Instead, we construct a case. We are masters at building the evidence, which is based both in realism (doing this plan would require capital I don’t currently have) and in arguments we make to obscure something deeper. From within the safety of that case, there’s no need to pursue the other thing. At least not right now.
Part of what makes the case so convincing is this: building your own thing requires a different kind of work than most high achievers have ever done. These are people who excel at operating within a structure. Give me the KPI, I’ll hit it. Give me the framework, I’ll master it. That is a real and hard-won skill.
Building something from scratch requires a different question: what is the framework? Do I have to build it myself? Not knowing what winning looks like before you’ve defined it is genuinely uncomfortable for people who’ve built their identity on knowing the answer. The case feels true in part because this part of it is.
Here’s the rub: the path they’re choosing instead may not be as secure as it looks. Spirit Airlines closed overnight. Whole divisions of companies have are being eliminated in a single budget conversation. The exec role that felt solid last year was gone by Q1. The certainty you’re trading the dream for was never guaranteed, and it is less guaranteed now than it has ever been.
In fact, at the end of the day, we are not guaranteed any tomorrow. Tim Denning uses this mindset to create what he describes as a “psychopathic sense of urgency:”
Whenever I try to delay priorities I tell myself “Timbo, you had a near-miss with cancer in 2015. What the hell makes you think you have the extreme privilege of being alive in three months to start this goal then?”
Without fail this thinking always makes me move faster. Believing you’ll be alive beyond today is sheer arrogance. It’s ego. And it’s bloody disgusting. How dare you. You could be dead tomorrow. So do it today or shut up and stop complaining
A psychopathic sense of urgency is a pattern interrupt. Use it.
He uses this as a way to keep himself focused. I think it’s also a useful way to tackle some of the objections in our case. My brain is excellent at spinning elaborate what-ifs (what if I fail, what if I do it and I hate it), and a surefire way to put those in perspective is to remind myself that the only thing I know for sure is I’m going to die, so if I want to do the thing, I better do it now.
As always, for every case, there’s a counter.
How to argue your case.
Like a good lawyer, you should be able to argue both sides. List every reason you can’t do the thing, then argue as opposing counsel.
I don’t have the skillset. I’ve only ever worked in one industry. Your honor, I object. Each of these skills can be put to good use building the thing you want to build. Any you don’t have, you can learn.
This isn’t the right time. For the jury’s consideration: what would the right time actually require that this time doesn’t have?
Building that would take way too many resources. Permission to cross-examine the witness: please list all the resources the current path requires. Then compare them to the other one.
You built the case. Give it a prosecutor.
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Powerful. I hope your friend listens. I immediately worked less hours when I started my own business. Made more money and ditched the commute.