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Engineering Generosity · Aug 13, 2025

A Week After Clarity? Uncertainty.

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Leo Guinan · Engineering Generosity

It’s amazing how much difference a week makes.

A week ago, I was sitting in the same coffee shop that I am right now. I was writing about accepting that everything I was doing was simply too far ahead of everyone, and I needed to slow down.

I’d discovered a love of coaching, and a realization that I’m truly able to help people in a one on one setting. And I had made the decision to set my research aside and focus on helping the people I could.

Hitting Reset on Life

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August 6, 2025

When I kicked off this stage of my journey in 2020, I had a lot of ambition, very little experience, and just enough insight to be exactly wrong about 90% of things. But with drive, determination, and plenty of stupidity to keep me going, I learned everything I needed to know. And I did so without any of the success that I thought I needed along the way…

And naturally, the universe decided to throw me a curve ball.

And a week later, I’m back in the coffee shop. But now, I’ve got choices to make that aren’t obvious. I’m now entangled in a game that I’d hoped to one day be part of, but had given up hope of participating in any time soon.

I wrote more about the game over here:

So here’s what I know for sure right now:

I love coaching, coaches have been the ones to change my life when information never was, and I have a specific transformation I’m able to make.

Coaches are the most undervalued asset right now because people don’t have a ton of extra money, so they don’t go looking for them. This means that coaches have to do more outreach to find clients than clients come looking for them. At least, until they have a big enough reputation to bring them in.

And most times, coaches don’t value themselves appropriately, because it’s a calling, not something they do to make a ton of money. If anything, they tend to pursue it for the sake of freedom.

That’s what made me focus on it.

All of this together shows me a need for a platform for coaches that takes care of finding leads, qualifying them, delivering them, evaluating their progress, and helping them and their clients decide when coaching is a good fit for both parties.

But, while the universe is seemingly yelling at me that this is the right course to take, I’m determined to stick to my slow and steady guns, and run the playbook I need to run. So if you’re a coach that is having issues finding clients, creating a steady enough income for yourself, keeping up with everything you need to do with the increasing complexity of the internet, or anything else that isn’t specifically your coaching, let’s chat.

If this does end up being the right path to go down, the first part of it is creating an agency offering that does everything for you. I’m basing it off of how I’m setting up my own coaching offer, and I’m now doing this for two friends’ coaching businesses.

I can handle one more coaching business on my own before I’ve got to start scaling the agency and bringing others onboard to help me, and I’m going to put it out on a first come, first serve basis.


I’m offering it for $5K/year, with that price locked in for life, with the full price being $20K with an annual commitment.

And finally, I’m going to end with a CYA, instead of a CTA. Nope, not “Cover Your Ass”, but “Choose Your Adventure”. I’ve been on a matrix kick, so let’s offer you a choice of the future you want for your coaching business.

Option 1: Take no action. Your coaching business continues the way it has.

Option 2: Talk to me for 15 minutes. Tell me a bit about your business and how it runs, and let’s see what happens. All it does is open up a possibility of a future conversation.

Option 3: Make a decision to give up your complexity on faith. Buy the available spot, because you see how your clients will be helped by you having the help you need.

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