This is a personal entry for my 30-day Trusting Myself challenge, part of Seth Godin's #Trust30 project, inspired by Ralph Waldo Emerson.

Today's Challenge:

What would you say to the person you were five years ago? What will you say to the person you'll be in five years?

Today's entry:

I just had a series of unpleasant job-interview flashbacks, so thanks for that, Corbett Barr.

Part of me knows that 5-year-ago me would never listen to now me, but for argument's sake, let's give it a go and pretend I'm not thick-headed. Five years is a pretty convenient timeline, since I just celebrated 5 years working for myself last month.

I try not to dwell one any one mistake, but if there was a pattern of mistakes when I started my business, it definitely revolved around second-guessing and letting doubts get the best of me. I suppose it's apropos, given the challenge, that my advice would probably be: "Trust yourself."

I can remember dozens of times when I had a short list of things to work on and then spent days or weeks basically just staring at it, because I wasn't absolutely sure any of those things would move the business forward. In hindsight, the steps to success weren't any one, obvious thing – they were a summation of small events and seemingly insignificant risks. I went to a networking event and met someone who, months later, saw my work on some blog and contacted me about a job.

The list goes on, but it has one thing in common – every success was built on choosing and doing. The cost of doing nothing was always higher than the cost of doing something, even if that something failed.

Thinking 5 years ahead is a lot tougher. If there's one thing I fear over time, it's losing perspective. I've had enough success to realize that fear and doubt never completely go away, and you can get lost in them. I know people making what most people would consider a small fortune, yet they still worry about money every day. Somehow, whatever they have, it's just not enough.

It's not greed – it's fear. It's also not just money – we can become slaves to both success and failure.

So, I guess I'd just remind myself why I'm doing this. I'm trying to live my life on my own terms, enjoy what I do, and spend time with my family. If I make money doing that, that's great, but I can't let success become a whole new kind of trap.