Entrepreneur Office Hours - Issue #178

Lessons from another finished (school) year

It’s late April, and, for me, that means I’ve reached the end of another school year. As I do my usual work of preparing final grades and saying goodbye to students who, in some cases, I’ve been working with for four years, I always find myself thinking about what I’ve personally learned.

Yes… what I’ve learned. Despite what most students think, their teachers learn as much as they do. Heck, I probably learn more.

This year was no different, so I thought I’d share my biggest learning. Or rather, my biggest learning in relation to entrepreneurship (which, I assume, is what most of you are interested in).

My biggest personal learning about entrepreneurship has been the value of doing less. I don’t mean working less or accomplishing less. I mean something more along the lines of “addition by subtraction.”

For example, in all of my classes, I removed assignments and lessons that’s I’ve been using for years. It gave students the ability to get more from the remaining lessons and assignments I kept because there was more time to engage with them. In one class I literally removed half of the assignments and doubled our focus on the other half. The result was the best class I’ve ever taught.

Outside of class, I did less, too. Again, I didn’t work less. I just mean I spent more time focusing on the projects that were more important to me and dropped a lot of the projects (and clients) that didn’t matter as much. Admittedly, dropping some of the work came at a financial cost, but the mental benefit has been enormous. I love what I do more now than ever before.

I’m sharing all of this because entrepreneurs have a tendency to always do more, more, more. I’m sure lots of you have that tendency, too, and, while it’s not inherently bad, it can cause more problems than most of us realize. Remember, as the old saying goes, sometimes “less is more.” As busy entrepreneurs, we often think we’re successfully wearing dozens of different hats, but the truth is we’re probably not nearly as good at it as we think.

In retrospect, I know that was the case for me. In fact, I didn’t realize just how bad I was at certain things (and/or how much I hated them) until I stopped doing them.

-Aaron

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Office Hours Q&A

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QUESTION:

NOTE: This question was posted on one of this week’s featured articles.

A fascinating exploration of the role naivety plays in the entrepreneurial journey. [Your article] highlights the dichotomy of how inexperience can both propel founders into action and cause hesitation. Embracing naivety as a catalyst for opportunity certainly provides a unique perspective on decision-making for aspiring entrepreneurs. However, I'm curious to know how you recommend balancing this naivety with the need for due diligence and strategic planning. To what extent should entrepreneurs rely on their inexperience to drive decisions, and when should they seek guidance from more seasoned professionals?

-Marshall

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I wanted to use this question as an opportunity to clarify something from one of my articles that might be a bit confusing. The article being referenced (the article you surely already read, right? 🤨) explores the important role naivety plays in startups. Simply put, startups are so unlikely to succeed that founders need to have a significant level of naivety (or, I suppose, denial) in order to pursue them.

One thing I didn’t mention when I wrote about the importance of naivety in a startup founder is the importance of something that counterbalances naivety: curiosity. Curiosity is a critical antidote for naivety in a startup founder. It’s what gives founders a chance at building successful companies because it helps them figure out the things they don’t know.

This relationship between naivety and curiosity is what’s going to allow me to answer Marshall’s question about the value of getting advice from experienced entrepreneurs. Founders don’t want to be naive and ignorant. They just happen to be naive and ignorant. There’s a big difference. People who want to be naive and ignorant don’t have curiosity and don’t want to learn. In contrast, founders want to know as much as possible about as many things as possible. One of the best ways to know more is to seek guidance from seasoned professionals.

In other words, the answer to Marshall’s question is that entrepreneurs rely on their inexperience to push them forward, but their inexperience also constantly pushes them to learn more. Connecting with experienced people happens to be one of the most efficient ways to learn more, so a good entrepreneur is constantly seeking the advice and guidance of seasoned professions.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!

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