I simply asked him “If you’re so smart with capital, why would you have time to manage mine?”

This wasn’t a caustic or sarcastic question. I wasn’t trying to give the guy a hard time. I honestly wanted to know why smart people who have the skills that can create wealth would use them for anyone but themselves.

This question isn’t unique to financial planners looking to pitch wealth management strategies. It’s salient to every would-be entrepreneur that at one point realizes they are actually losing money by working for someone else.

It’s the salesperson who realizes that they are responsible for more of the companies’ revenues than the CEO is. It’s the recruiter that does the math and realizes they are giving away 66% of their income because someone else is paying the phone bill. It’s the marketer that concludes that without their marketing acumen, their client’s product would have never sold a single unit.

Stop Selling the Map

At some point we all need to ask ourselves what’s keeping us from owning the pie instead of just taking a bite out of it. If our guidance among clients, colleagues and partners is so spot-on that we truly are incredibly valuable, then aren’t we doing ourselves a huge disservice by just giving that all away?

I asked myself the same question when I was running an interactive ad agency named “Blue Diesel”. For years I would run into client’s board rooms with big ideas for how to take advantage of the Web. We’d drag our clients kicking and screaming onto the Web, only to see them build incredible businesses on-line.

Yes, we got paid a fee along the way. But at some point I had to be honest with myself – if I knew so much about creating opportunities on the Web, why was I selling them to someone else for a fee? That’s like knowing where a huge pot of buried treasure is located and selling maps to other people to go find it.

Try before you Buy

Of course deciding to start your own business isn’t just a simple mathematical equation. There’s a great deal of risk involved with any new endeavor. But the true risk that entrepreneurs are most worried about are the risks associated with not trying their hand.

Fortunately there are ways to test your skills before you take the plunge.

One way to test the waters is to look for opportunities to swap your fee for a piece of the equity in the venture you’re working with. This is truly an at-risk proposition that provides some of the risk and reward of starting your own company without quitting your job to do it.

Another way is to launch a side project, assuming it doesn’t conflict with your current obligations. Many great startup companies have started as side projects that employees dabbled with until the side job became their main job.

However you test the waters, the goal is to truly test yourself. No matter what the outcome is, you actually win.

If the new venture takes off, then you’ve proven to yourself that you truly have what it takes to own your own destiny from top to bottom. If the new venture flops, you can feel confident that you are maximizing your value inside of your existing organization (although if you’re really meant to be an entrepreneur, you’ll just keep trying until one of those ventures succeeds!)

The Ultimate Test

This isn’t to say that running your own company is the only way to test your skills. Jack Welch ran GE as their CEO for 20 years and I’d say he was a pretty capable guy. There are lots of opportunities to prove your skills that don’t involve launching your own company.

Yet in many ways, betting your own fortune based on your own skill set is the ultimate capability test. A financial planner that can take a small pool of their own capital and turn it into a mountain of wealth has clearly proven not only their capabilities, but their belief in themselves.