Here we are on Day 3 of #500DaysTo50. I’ve been trying at this “career thing” for over 25 years now. If I’m asked the “what do you do” question now, I’m answering that “I’m an entrepreneurial web developer and online marketer”.

That’s largely in keeping with how I’ve made my career. I formed my first company in 1996, my first successful company in 1999, and I’ve pieced together a bunch of other things since then based on my interests.

One thing that has been an absolute constant for me is learning new things. And I realize a lot of that learning has been based on fixing gaps that were exposed in embarrassing ways.

While running an online marketing agency, I didn’t have any real coding skills. One of our offerings was helping companies make sure their new websites were going to work well for SEO and SEM efforts. While we were great at that, we weren’t qualified to look through the actual PHP code our subcontracting agencies built for the websites. When our client’s site was due to go live, it turned out almost zero work had been done on the site, and we were able to launch exactly one page of the site.

I swore I’d never let that happen again, and I learned PHP and the LAMP stack to be able to make sure I could be better prepared. I now develop WordPress sites for clients as a result. They do very well with the search engines due to my previous experience.

Along the same line, in a business development meeting, I once said, “You can just give us access to your database, and we can build the sites automatically for you.” The CEO of the other company rightly replied, “Well, we’ll never give you access to our database, but we have an API.”

I almost shut down my company at that point, but I chose instead to learn more about MYSQL and other databases and how APIs operate.

But maybe I should have simply hired people who knew a lot more than I did to cover those weaknesses I had. I’ve spent about 5 years re-tooling instead, as I’ve always been disappointed that I couldn’t code. That’s meant a lot of financial sacrifices. Nobody I know would consider them smart career moves.

But that’s how I work, and I can’t see myself stopping. It’s a Sunday morning, and I’m going through a course on ReactJS for a couple of big projects I have thrown myself into. I have others helping along the way, and I’m able to make a few small contributions as I get up to speed.

It’s entirely possible my fear of public embarrassment has shaped my career in completely unreasonable ways. My hope is that the payoff in the end will be huge to make up for the lost time. We’ll see…