Are You a Serial Opportunist?

A term that I see getting thrown around on an increasingly frequent basis, especially among all my other self-employed friends, is “serial entrepreneur.” You’ve probably seen it in the context of Internet marketing, dot com startups, and other related industries.

The idea is that this person, this professional is not necessarily married to any one job or any one company. He or she will start with one business, grow it to profitability, and the move on to another endeavor entirely. And this cycle repeats itself over and over and over again over the course of several years. Some ventures work out great, while others fall flat.

Oftentimes, a significant part of the motivation for this “serial entrepreneur” to abandon an existing endeavor to pursue a new venture is a perceived sense of opportunity. The grass is always greener on the other side, so they start to chase this new pasture with the hope that it’ll bear more success. But is that really the right way to go about things? Are you moving forward or are these just a series of lateral movements?


A good way to visualize this kind of journey is by imagining a rock climbing wall. Your ultimate goal is to get from the ground all the way up to the top of the wall. In this particular case, your long-term objective is perfectly clear and easily seen. Of course, this usually isn’t the case when you look at your professional career.

As you begin your ascent, you reach for the various rocks and notches. You put your left hand there, your right hand there, your left foot there and so on. In the short term, you might see that a particular hold is easily within reach. However, if you take on a longer term perspective, you might come to realize that moving in that direction is ultimately counterproductive, because it does not lead to a better path toward the top of the wall.

Instead, there might be a different protrusion on the wall, just outside of your immediate peripheral vision, that will lead to a better path. If you take the route of the immediate opportunist, you’d grab that first hold and find yourself in no better a position than you were in previously. If you look at the bigger picture with your final end goal in mind, you’re more likely to grab this second protrusion instead.

How can you apply this line of thought to your online business? Allow me to provide you with an example from my own professional life. All too often, I get very caught up in client work as part of my freelance writing business. Each individual project yields an expected and near-immediate payday. Write these posts or these articles to receive this amount of money.

However, I have to ask myself whether working on these projects is really moving my career forward and in the direction that I want to take it. If I want to write more e-books, for example, does it make sense for me to take on a copywriting gig with a local plumber? It might make sense in the short term, helping to pay my bills, but it might not make nearly as much sense in the long term. I’m only jumping on that opportunity because of the (near) instant gratification of a paycheck.

In taking on work like that, I may suffer from opportunity cost. I’m spending time writing about plumbing, failing to invest that time in my own business or my own projects. I’m favoring short term gains over long term goals.

Absolutely, there is a strong temptation to strike the pan while it’s hot. Absolutely, you are going to be motivated for an immediate payday, because you’ve still got day-to-day living expenses. It’s awfully tempting to jump on the latest social media trend and “cash in” while you can, but will these projects help you make more money in the long run? Maybe not.

Even though the upfront cost of a great press release, a terrific landing page, or an incredible new blog design may not yield immediate returns, these are investments in the long-term future of your business. You really do have to ask yourself. Are you merely surviving the day-to-day grind? Or are you really building toward something bigger and better? Are you getting any closer to the top of that wall?

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