How to Figure Out What You Should Do as an Entrepreneur

Hindsight is more than just 20/20, it’s a tool for your future

I’ve always been a writer. More specifically, a blogger. While maintaining an award winning travel blog for ten years, I thought I might be able to replicate that sense of community and notoriety around a personal blog as well. But it only took me one year to realize I couldn’t replicate it through a personal blog because it’s just too personal.

I abandoned the idea in exchange for writing on a platform that already had it’s own community — this platform. It’s like a vacation home here, all I had to do was show up with my suitcase and move in.

While on “vacation” I never let go of my two blog properties. I’ve kept the travel one alive online because it’s still a valuable resource for thousands of readers. And I kept the personal web space because it’s a great custom domain name for me as a writer, even if it’s just been sitting around collecting dust for a couple of years.

Recently, I revisited the dust and tumbleweeds of my writer web space, trying to come up with ideas to revamp it. Having abandoned it long ago, I never gave up on the idea that one day it might have a new purpose, a business purpose.

After spending more than a year marinating in ideas about exactly who I would like to be as a writer, I have finally figured it out. All I had to do was look at my lonely web page — a spectacular photo of myself overlooking a never ending vista of the Caribbean sea.

The idea of who I used to be and who I could be, came flooding into my mind.

Go with what you know

It’s crazy that it took more than a year to figure this one out. It really is as simple as “go with what you know.” The challenge lies in figuring out what you do know well enough to build a business around.

Each of us knows how to do something that no one else knows as intrinsically as we do. Once you identify that particular chunk of knowledge, you can begin the task of dissecting it into bite-sized, deliverable pieces.

In my case, abandoning my blogging career for a long time was the only way to decipher what my saleable knowledge actually was.

Not only was I a travel writer for a long, long time, I now have the elemental skills needed to build effective communities around the trade. I have fundamental expertise in how to execute the craft. And I have inside information gained solely from my own trial and error. Nobody else knows what I know because no one experienced it the way I did.

My knowledge is so much more than those just starting out on the same path.

I learned what I didn’t want

It’s funny how you can figure out what you don’t want by doing what you thought you wanted.

Throughout my career I adored the writing and traveling aspects, but as my reputation morphed into its own beast I realized that I did not want to be everyone’s ticket to free advice. It’s overwhelming, as I previously wrote in this piece.

I could have never figured out that I didn’t want the influencer life unless I had lived through it. This is one aspect of writing that newbies starting out may not consider, which is another teachable component.

Each little stumbling block from the past turns into a foundation to build on for the future. No matter what piece of knowledge you have acquired in your area of expertise, it is something that not everyone is privy to.

The people will show you what they want

Perhaps the most interesting aspect of letting go were my observations after the fact. If you were any good at what you used to do, the people will keep letting you know.

Having left my web space intact, I have and still do receive regular emails from those who stumble onto my site. They still ask questions, they still want answers. I call it research, only I don’t have to actively do it because they’re serving it up to me on a silver platter.

Are you catching on yet? I’ve been taking notes. Lots and lots of notes. This is a buildable tool and another teachable component.

I learned what I actually wanted

This is perhaps the most important slice of the pie. After retiring from what I thought I loved doing, and letting it turn to dust and tumbleweeds, there was a gaping hole in my life that had always been filled by “doing.”

I came to a point where I had a bit of regret. I wished I’d known everything I now know, when I started out so many years ago. I wished I’d had systems in place from the start because it would have made the journey so much more practical and fruitful.

As I have learned, there’s no way to figure anything out until you put in the time doing it. It is only in doing that you begin to see patterns and figure out ways to streamline your work.

Another key point I learned was that I did want the travel part of my job, but I did not want the commitment part. In the last few years of my career I found myself resenting the obligation aspects of my work, because that took the pleasure out of the enjoyable parts.

When this happens in any job, it’s a clear sign that it’s time to move on.

What do you do after you’ve decided to move on?

The answer is simple. You fill the gaping hole of “not doing” by changing gears. You gather the pieces you loved most about your past work and build them into a complete new structure to move forward with.

Letting go of the old and latching on to the new and improved is something that can only be achieved through time and distance away from it.

When you leave any career, the whole thing doesn’t have to go down the tube. By allowing yourself the space and time away from it, you’re eventually able to realize what you loved most about it and why.

And that? It’s the sweet spot we should be aiming for when considering any new business venture.

In my quest for personal fulfillment I have become highly adverse to the idea of people doing work just for the money, or doing work they’re not passionate about simply because it’s what they’ve always done.

If you lack desire in your chosen area of work, your absence of heart will shine through. We can’t excel at anything we don’t truly love, and we can’t sell what we don’t believe in.

It’s never a win when you’re just letting the wind and sails guide you. We need to take the wheel, steer the boat, and let passion propel us.

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