You step onto a boat. It feels different—but you expected that, because you’re on the water. And while you enjoy the next few hours (or days) on the boat, you don’t really think about what it will be like when you step onto dry land.
When you finally step onto land, it’s apparent you’ve developed “sea legs” because you still feel like you’re moving, even when you’re not.
It’s not like you’ve never walked before. It’s not like you don’t know that you’re now on land. You just can’t out-think the reality that your brain and body got used to the water and now you’re back on land.
I know my title says this post is about entrepreneurship. Trust me, I’ll get there.
But here’s what I want you to think about…
Let’s say you head out onto the water the next week. Or the next month. Or the next year. Let’s say you spend a few days on a boat again.
Now imagine getting back onto land.
You know what happened last time. You’re prepped. You do all that you can to prepare yourself for the situation. And then you step onto land. Guess what happens? You still feel like you’re moving. Don’t you? Even though you knew it was coming. Even though you were prepped. Even though you had experience.
This is how I explain entrepreneurial efforts to folks who have worked in a single startup and are planning to do it again.
Every one of them assumes that because they’ve done it once before—even if they had success the first time— they’ll be better prepared the second time around.
Here’s the reality: Entrepreneurship isn’t easier the second time.
Here are 3 reasons why it’s not any easier and what you can do about it:
- Your success last time was not just about you. You were lucky. I know, you don’t want to hear it. But your theme company or your plugin company showed up at just the right time. The world was different four or five years ago.This time around, the competitive landscape will be different. So don’t trust that what you bring to the table is enough. Get some help to analyze your market and figure out the best way to differentiate yourself.
- Your expectations are higher. Admit it. When you last created your little theme shop, all you hoped for was enough extra money so that maybe you could take a nice vacation. When it grew bigger and you even hired someone on staff, you were pleasantly shocked! Now, after years of running that kind of business, you don’t have the same kinds of hopes. You want a home run. But the odds haven’t gotten any better. So you’re more likely to be disappointed. And that may lead you to quit when things get rough (and they will). Talk with those closest to you to help you set reasonable expectations.
- Your memory is failing you. Can I tell you a secret? The last time you started something, you worked like a dog. I know, it’s hard to remember those days. If it’s been a while, it’s hard to remember how many different times your shop almost closed.
These days you want to work, even work hard, but you may have forgotten exactly how many nights you were up forever. So before you start a second run, spend some months helping others. Rest. Build up an arsenal of favors. That way, when you do start something, you can ask others to join you in helping you run at that hill again.
I’m not trying to tell you not to quit your gig and start a new company. I’m not trying to tell you that your next plugin idea will suck.
I’m simply suggesting that it won’t be any easier because you have experience. At least not the second or third time. I discovered I didn’t really get used to things until my 4th startup. So startups #4 and #5 benefited from experience, but #2 and #3 were seriously challenging.
Work hard. Make friends. Get help. Find perspective.
And most of all, rest and plan for the battle, because it will be every bit as hard as it was the first time you did it.
Chris Lema is the VP of Software Engineering at Emphasys Software, where he manages high performers and oversees product development and innovation. He’s also a blogger, ebook author and runs a WordPress meetup in North County San Diego. His coaching focuses on helping WordPress businesses, or businesses wanting to leverage WordPress.
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