Why Learning From Doing Beats Learning From Books

I'm sitting in a coffee shop right now, writing this on what feels like both an ending and a beginning.

Today is the last day I'm operating my current business, Tuckedito. After 4.5 years, this cycle of my life is coming to an end. I had a newsletter ready about practical automation for small business (definitely more aligned with where this blog is headed), but that felt like it should wait. This needed to be written today.

When I look back on these posts later, I want them to capture what I was actually learning and thinking about in real time. The lens is simple: what value can I pull from what I'm currently experiencing and share in long form?

Sometimes raw insight provides the most value, even if it's messy. At the very least, it's valuable to present me and hopefully future me as well.

What 4.5 years of building taught us

My brother and I knew absolutely nothing about the industry we dove into when we started Tuckedito. We knew some things about business, but only from reading, watching, and listening. Not from actually doing.

I learned later (from doing) that these learning methods are much different than learning from doing. Funny how that works.

But diving in and figuring it out while building did work for our business. Plus I learned how to cook well, which wasn't exactly in the business plan.

We built something successful and created so many memories together. We met people we never would have encountered and ran into old friends who might have forever remained just another face in the yearbook.

On the business side, I'm taking a ton from this first stage.

I can now see frames that I could never have pictured without direct experience. I know what success looks like. I know what unnecessary looks like. I know what "absolutely don't do that" looks like.

For example: don’t just do the books in your bookkeeping system without reconciling with the actual numbers in your accounts (there could be a number of duplicate transaction you just approve that cause a huge headache later on).

Exiting in the black, entering the unknown

We're closing this chapter in the black, with the opportunity to move on to stages of life we dreamed about four years ago.

There's still nervousness and uncertainty, but mixed with that is so much excitement and hopefulness. This tells me we're personally on the right track. The excitement in the last business had mostly ended, and it's good to get that feeling back. But we definitely wouldn't have reached this point without completing that four-year cycle.

Our minds are different from four years ago. Much different.

They give us the ability to visualize opportunities we can actually pursue now. The visualization of these opportunities generates the excitement that will drive us forward.

Jumping in again, but differently this time

My experience of learning by doing with Tuckedito is partly why I'm jumping into Simple Flo the same way I jumped into Tuckedito. I've studied and learned for over a year, and now it's time to figure it all out while doing, again.

It worked the first time. I figure it will work again, but who knows?

At least this time I have four years of real-world business experience behind me rather than five years of doing what I was told at billion-dollar corporations. I feel more prepared because I have an internal compass to navigate the seas of uncertainty and find the island of value, both for myself and future clients. After 4 years of ultimate responsibility for my decisions I’ve become a better decision maker. It’s something you just don’t experience in the corporate role as an entry or midlevel employee.

I'm sticking to the principle that necessity is the mother of invention. I have a good foundation laid. I have a business model and some new skills. I have a practical lens and an eye for business. Now necessity will push me toward selling the vision I see to others who I believe will benefit from it.

Coming full circle to the original vision

This new business alignment is closer to what we envisioned at the start of Tuckedito.

When we started 4.5 years ago, we'd been listening to Tim Ferriss podcasts for like three years and were dreaming of some sort of digital business. But we didn't have the skills or money to start it at the time, so we jumped into something we could actually conceptualize and execute.

Now we have new tools, better skills, and a business foundation built to operate in the world we wanted to operate in years ago.

The cycle feels complete, but also like it's just beginning.

Let's see what the future brings.

I'll be sharing more of the journey as it unfolds, probably with the same mix of uncertainty and excitement that got us this far in the first place.

If you've been through your own business cycles or are contemplating a jump into something new, I'd love to hear about it. Sometimes the most valuable insights come from comparing notes with fellow travelers on the uncertainty highway.

Thanks for reading,

James

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