What mistakes are you willing to make?
If you’re anything like me, you really want to do things right.
And this desire to do things right can make it hard to navigate Should vs. Want conflicts, aka situations where you WANT to do one thing, but you feel you SHOULD do something else.
I think I should go to bed around 10 or 11 and wake up around 6 or 7….
But I want to go to bed around midnight or 1 am and wake up around 8 or 9.
I’ve heard that I should follow a certain series of steps to most effectively scale my coaching business…
But I want to skip some of those steps and jump straight to the part I’m most excited about.
I’m currently working on building a digital course for all of you. I’ve been told by experts that I should pre-sell the course before making it and then make the content week by week while I deliver it…
But I want to make the whole thing first and then sell it and deliver it.
How do I know whether I should do what I want to do, or what I should do?
I’m terrified of flouting conventional wisdom.
It always seems to be coming from wise experts who really know what they’re talking about and have helped thousands of people before me achieve all their dreams.
In the face of all that ✨wise expertise✨, how do I know that my wants aren’t lazy or self-indulgent or stubborn — or just plain STUPID? (My biggest fear.)
This is the question I ask myself to navigate these (admittedly scary) Should vs. Want conflicts:
What mistakes am I willing to make?
If I make myself go to bed at 10 pm, the potential mistake would be that I interrupt my flow. I’m a night owl, and I do some of my best thinking in the evening.
If I let myself go to bed whenever I want, the potential mistake would be that I’m running a bit behind on my routine in the morning. I’m never late or unprepared for calls. It’s just that I’ll be a bit rushed with showering and getting ready.
Between those two, I’d rather make the mistake of running a bit behind on my morning routine than make the mistake of interrupting my flow.
I’ll gladly OWN the mistake of running behind in the morning — it doesn’t seem like that big of a deal, especially in comparison to staying in flow.
I don’t want to live in a world where I’m consistently losing my flow. It’s too precious to me, and I’m happy to risk other mistakes to protect it.
If I make myself follow the suggested sequence for scaling my business, the potential mistake would be that I force myself to offer products I’m not excited about. Also, that I develop an overall habit of doing what I’m “supposed to do” in my business rather than developing a habit of making my own decisions. (Not a great habit for a CEO!)
If I let myself scale my business the way I want, the potential mistake is that it takes me longer to make the new product a success. It’s also possible that I try for a long time, come to realize the conventional wisdom is correct, and change my strategy.
I’m happy to make the second set of mistakes.
I’m happy to take a “longer and more inefficient” path to success, if it means that I’m learning and sharpening my own instincts as I go.
And I’m happy to realize I was wrong and change my approach (as long as I’m doing it because I’ve genuinely changed my mind, not because someone else told me to).
But I am NOT willing to make the mistake of forcing myself to do something that doesn’t feel right to me. That’s a surefire way to build a business I hate.
If I make myself pre-sell a course before making it and then only make the content a week before I deliver it to clients, the potential mistake is that I market & sell something I don’t believe in and then deliver it in a way that doesn’t feel right to my creative instincts.
If I let myself make the whole course before I sell and deliver it, the potential mistake is that I have to re-make the course multiple times because I realize, through the selling and delivery process, that it wasn’t quite what people needed.
I’m totally happy to make the second mistake. If I make a full course, deliver it, and then burn it down and make a totally different course several times… Sounds good to me!
To me, that’s not inefficiency or wasted time. That’s the exact kind of robust learning and product development I’m here to do.
(And I’m going to continue to offer one-on-one coaching in addition to the course. The product that’s working is going to continue generating revenue, which gives me plenty of coverage to develop the new thing exactly the way I want, even if it’s “inefficient.”)
Trying to do it right is a stressful standard.
Every path has potential mistakes — and you’re too smart to NOT see the issues with all the paths in front of you.
So rather than trying to find the path with no pitfalls (it doesn’t exist)…
Frame the decision as a choice between two potential sets of mistakes.
Things can end up going totally screwy, no matter what you choose.
Information is imperfect. You don’t know what you don’t know. None of us know how this story is going to end.
But you can decide ahead of time which flavor of screwiness you’d prefer.
And then you can relax and enjoy this crazy ride.
Because you’ve committed ahead of time to the set of mistakes that is most in line with your values.
This is a process we can go through in depth if we work together.
You don’t have to make whatever decision you’re trying to make all in one day. You can take your time.
We can really flesh out the potential mistakes on both sides.
We can think deeply about your values, your North Star, and what you’re really solving for here.
We can find ways to do experiments and gather data before making a final decision.
And then we can keep evaluating and adjusting even after the decision is made.
(Because life is not “set it and forget it.” New Should vs. Want conflicts are going to keep popping up.)
If you want to carve out the time and headspace to really be thoughtful about the decisions you’re making and feel assured that they’re taking you toward a life you love (not a life you hate, or merely tolerate)…
And if you want to do that with an expert thought partner who can see your blind spots and draw on hundreds of hours of experience working with people just like you…
Then come talk to me, and let’s get started :)
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