The Tricky Line Between Persistence and Stupidity

Entrepreneur Office Hours - Issue #267

I just encountered my least favorite cliche in entrepreneurship. I was sitting in the back of a room listening to someone giving startup advice to a group of entrepreneurs, and he was telling them that, “Great founders never quit.”

Ugg… it’s terrible advice because it’s situational. In some situations you definitely shouldn’t quit. But, in other situations, you absolutely should. More importantly, how do you know which situation you’re in?

Unfortunately, there’s not a good or guaranteed answer. But, I’ve developed a decent rule of thumb, and I thought I’d take a moment to share it.

In general, when people are talking about persistence in entrepreneurship, they’re not talking about persistence in the context of any one specific project, idea, or venture. They’re talking about persistence on a macro level… a Gladwellian 10,000 hours kind of thing.

For example, your individual startups might fail, bot that’s OK. Persistence isn’t about not giving up on a bad startup idea. It’s about not giving up on your broader entrepreneurial ambitions. It’s about starting another startup, and another, and another until your persistence turns into a meaningful education that ultimately helps you achieve success.

Hope that little bit of advice is a helpful for you as it’s been for me… particularly over the past few years of my startup journey as I’ve started to better understand the longer term experience and roadmap of what it means to be an entrepreneur.

-Aaron

---

---

This week’s new articles…

Maybe Entrepreneurs Should Be More Careful About What They Wish For

Entrepreneurs are great at dreaming big, but they’re not so great at appreciating the realities of those dreams.

---

---

The Most Overlooked Ingredient in Entrepreneurial Success

Being a successful entrepreneur requires cooking up something you’re probably not going to like

---

---

Office Hours Q&A

———————

QUESTION:

Aaron, I’m considering leaving my current job to work on my startup full-time, but I’m torn. On one hand, I worry about the financial risk and losing my stable salary. On the other hand, I feel like my startup could grow faster if I dedicate all my energy to it. What’s your take on how to decide the right moment to go all-in on a new venture?”

-Taylor

----------

This type of decision hinges on a few key things: your personal financial situation; the traction your startup already has; and, frankly, how miserable you are trying to juggle both worlds.

First, let’s talk finances. If quitting your job means you’ll be stressing over rent every month, that stress could severely impact your focus and productivity. A little pressure can be motivating, but if you're in full-on survival mode, thinking creatively or strategically gets real tough. Make sure you’ve got enough runway — savings or other sources of income — to give your startup a real shot without living in constant fear of running out of money.

Next, look at your current traction. If your startup has even a small but growing customer base and you can see clear steps to scale, going all-in might be exactly what you need to accelerate. But if you’re still tinkering with your idea and don’t have much validation yet, you might be better off keeping that day job safety net until you have a stronger foundation.

Finally, consider your mental bandwidth. If splitting your time is causing major burnout or slowing your startup’s progress significantly, that’s a sign. Sometimes, not giving your new venture the attention it deserves can be just as big a risk as going all-in.

Ultimately, finding the right answer here requires finding a balance between calculated risk and practical planning. You don’t want to hang onto your day job so long that you miss your window of opportunity. But you also don’t want to jump too soon and sabotage your chances by running out of resources.

Hope that helps you think it through the issue, and best of luck making the call! Sorry this answer isn’t more definitive, but, the truth is, these are never “one-size-fits-all” types of situations.

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