This week’s host is James Serra, and he continued the stream of super hard questions from a personal standpoint that I and then Pat Wright started this year off with, as he asks what risks we have taken in our careers?

Of all the topics in the world, I may be sort of the worst person to answer this question. I’m not a risk taker, and I didn’t grow up in a particularly risk-taking family.

My father took one big risk in his career, quitting the job he had always loved because of a dose of nepotism. The risk paid off in and his career took off in the years until he passed away quite early. While I did learn some great lessons in life, risk-taking just to take risks never even really came up. Taking a principled stand, working hard and trying to be the best at what I do, definitely.

Ok, so maybe I might be the one who is a bit conservative in his career rather than a bad person to answer.

I’m not completely risk-averse

Honestly, I have really only taken a few risks career wise. And those risks have always paid off in some ways, but never in the ways I had hoped. In fact, in so many things I have done that required risk, I have always come in at the tail end of the glory days. Take book writing. Just before I started that adventure, authors were making grand amounts of money. My first book, I got a healthy amount of advance. Then the internet really started making books less and less valuable. (And I am still always up for a long-form book project… despite the far lower amounts of money most books make today.

Book writing is career adjacent, but in this post I want to focus on strictly primary job risks. And as I’ve spent 25 years over three distinct stints at the same company. You can imagine that either I was lazy, or a did it for a reason: I’ve been very happy there and they have supported me in my community endeavors as long as I am sharing it with them, so why take a risk?

But as I noted in an editorial I wrote for Simple-Talk, everyone has a price. I keep a mental list of the places that I would leave again without coercion (that list is very small and narrow, mind you, but it does exist along with some strict terms and conditions!)

The two times in my career where I took a big risk follow.

First try: education startup

Back in the late 1990’s, a friend left our company for an education startup in Nashville, Tennessee. It was the tail end of the dot-com bust, and I had some stock options that the old joke was that they were worth less than toilet paper. This was completely not true, since we didn’t even have paper versions of these stock options. Like most failed risks, the value was learning things. I learned a lot about being a DBA, how companies go from “great ideas, great backers” to “well, this might not have been a great idea after all.” If anything, it probably made me more risk averse.

The company I had left for the new job needed someone in Nashville, so when that job ended, I got my first opportunity to manage a call center (At least temporarily). I went back to being a database developer/DBA and later an architect until the call center was fully built out and proper staff were hired. What I did not learn was much about managing telephony hardware.

Second try – editor

About four years ago (twenty years after my first try), I got a chance to make a fairly drastic career change and finally get my chance as a full-time writer/editor. It was for a software company I love that did a lot of great things for the community (and still does, for that matter, as they were a sponsor at DataTune in Nashville last week).

Over the time I was there, several other software companies that had similar offerings had removed similar offerings. Fortunately for the community, the resource I managed continues, but there were cutbacks. I still love the company and have recently published several articles for their learning site. But again, my timing wasn’t great.

I learned about marketing a lot more by being a part of a large marketing group, but what I truly learned was how to be a better writer and programmer. My focus was to expand the offerings and bring in new writers. Working with 15-30 writers at a time, with a lot of them new to writing, has helped me to understand what makes a good blog and to try to do my new blogs better than before.

In the end, why take risks?

Here is my challenge to you. Ask and answer that question before you take risks. And unless you can truly answer why you should NOT take the risk, go for it. And being afraid alone probably isn’t a good enough reason. There are many reasons not to take a risk (don’t jump out a plane without both a parachute and the knowledge to use that parachute!), but only you know if the risk has the potential to be worth it. And as I note, even my limited experience with failure taught me a lot.

After reading the rest of this blog, you might have expected me to go the other way. Wisdom comes with looking back at the experience you have in life.

When I went back to the same company for a third time, it started with me considering quite hard, “Based on everything you know about all the other companies, where should I work?”

I even had to really make sure I wasn’t just going the path of least resistance because I was lazy or just avoiding risk. I will also admit I am definitely a loyal person, but as I noted in that blog, I know the limits of corporate loyalty. In the states I have always worked in, I can leave my job any day for (almost) any reason, on my side or theirs. Part of the reason is that I get time to learn, share with the community, and do something that I believe is worth it.

So career risks? I have never sought them out, but I am not suggesting you shouldn’t. Every step I took I generally knew what I wanted to do, and a large part of it has always included doing just what I am doing right now. Spending my afternoon after a conference at a coffee shop writing, and then going back to work the next day, building the best software I can.

Do I have any more risks left? Who knows? I clearly don’t see them out, but I don’t always say no either.