I hosted this month’s T-SQL Tuesday invitation in which I asked, “What career risks have you taken?” I got some great responses which I’ll recap here,

Career risks? Rob Farley

Rob took an interesting angle on the idea of career risk. In his post, he reflects on how for much of his early career he actually avoided risk. After finishing university, he chose stability over uncertainty — turning down a PhD and opting for a steady consulting job instead. Even when he moved countries (Australia to the UK and later back again), he gravitated toward permanent roles because he had a young family and valued security. It wasn’t until more than a decade later that he took what he considers his biggest career risk: starting his own company in 2008. But what really stood out to me in Rob’s story is how he defines success. He isn’t trying to build a startup to sell or chase investors. Instead, he built a consulting business that reflects who he is — heavily involved in community work, volunteering time to help others in the data world, even when it doesn’t directly generate revenue. Some might call that “commercially naïve,” but Rob frames it differently: the real risk would be building a career that forces you to be someone you’re not.

T-SQL Tuesday #196 – What career risks have you taken? by Jamal Hansen

Jamal shared a perspective on career risk that I think many of us recognize. In his post, he reflects on how his career evolved through a series of smaller decisions rather than one big leap. Early on, he leaned into opportunities to learn programming and technology, gradually moving deeper into the data space. The risk wasn’t a dramatic career pivot but a willingness to keep exploring new skills and directions even when the path wasn’t perfectly defined. What stood out to me is that Jamal frames risk as a mindset — choosing curiosity and growth over staying comfortable. It’s a good reminder that many careers are shaped not by one bold move, but by a steady pattern of learning and adaptation.

T-SQL Tuesday #196: What Risks Have You Taken in Your Career? by Louis Davidson

Louis took a refreshingly honest approach to the topic: he openly admits he’s never really been a big risk-taker. In his post, he reflects on two moments where he did step outside his comfort zone. One was leaving a stable role in the late 1990s to join an education startup during the dot-com era—an experience that didn’t work out financially but taught him a lot about how companies succeed or fail. Years later, he took another leap by moving into a full-time writer/editor role at a software company, gaining valuable experience working with writers and the broader community. What stood out to me is Louis’s takeaway: even when risks don’t pay off the way you hoped, the learning still matters. Sometimes the value of a risk shows up years later.

T-SQL Tuesday #196: What Career Risks have you taken? by Pat Wright

Pat took a thoughtful angle on career risk by focusing on the kinds of opportunities that stretch you professionally. In his post, he talks about stepping into roles that involved organizing events, speaking publicly, and getting more involved in the SQL community. Those aren’t always the risks people think about when discussing careers, but they still require putting yourself out there and being willing to grow. What stood out to me is how he highlights the value of community involvement as a career investment. Sometimes the biggest risks aren’t changing jobs or companies — they’re raising your hand, sharing your knowledge, and becoming visible in the community. Over time, those choices can shape a career just as much as any job change.

T-SQL Tuesday #192: What career risks have you taken? by Mala Mahadevan 

Mala shared a story shaped by a simple belief: the work you do every day should actually fit who you are. In her post, she reflects on a career that has evolved through several transitions—starting as a COBOL programmer, moving to VB, then SQL Server DBA, later Database Engineer, and now Data Engineer, with plans to move toward AI ethics. Along the way she took risks that meant stepping away from roles where she was already comfortable, including leaving a long-time DBA position and relocating for a new type of engineering role that better matched her interests and reduced burnout. What stood out to me is her perspective that career choices aren’t just about salary or stability—they’re about protecting your long-term well-being and continuing to grow.

T-SQL Tuesday #196 – Two risky career decisions I made by Steve Hughes 

Steve shared two career decisions that ended up shaping his entire path. Early in his career, he took a risk by moving into consulting after building a warehouse management application using Access, Visual Basic, and barcode scanners—jumping into a world where he had to grow quickly and solve real problems for clients. Years later, he took a different kind of risk by stepping out of consulting to join a client company so he could spend more time with his family instead of constantly traveling. What stood out to me is that both decisions were about more than just career advancement—they were about building a life that balanced work and family. Looking back, Steve says it was absolutely worth it. Sometimes the right career risk is the one that protects what matters most.

T-SQL Tuesday #196: Career Risks by Andy Yun 

Andy shared a story about a career move that surprised even him: going into sales. After years working as a SQL Server developer and DBA—firmly in the “hardcore techie” camp—he received an unexpected message asking if he’d consider becoming a sales engineer at SentryOne. At first, he wasn’t even sure what that role meant, and like many technical folks, he had some pretty negative assumptions about sales. But he decided to give it a shot, largely because he respected the company and its community-focused culture. What stood out to me is how that leap challenged his own biases. Sometimes the risk isn’t changing technologies—it’s changing how you think about entire career paths. I also add his story is very similar to mine – going from a software developer to a pre-sales role at Microsoft. But I love the job as I am “teaching” every day and am partnering with my customers to help them successfully build solutions.

T-SQL Tuesday #196 – What career risks have you taken? by Chad Callihan

Chad took a perspective that many people experience but don’t always talk about: the risk of staying when companies go through acquisitions. In his post, he describes starting at a small company of about 100–150 employees, which was eventually acquired by Cerner and later by Oracle, turning his workplace into part of a massive organization. Each acquisition brought uncertainty—new leadership, new priorities, and the question of whether it still made sense to stay. What stood out to me is that Chad frames staying put as its own kind of risk. We often think the bold move is leaving a company, but sometimes the gamble is riding out the change and seeing where it leads. Careers don’t just change when we move—they also change when the company around us does

Risks? I’ve Taken a Few by Mike Walsh

Mike shared a story that feels very real to anyone whose career path didn’t follow a perfectly straight line. In his post, he reflects on several risks along the way—leaving a stable role to pursue consulting, navigating a difficult business partnership, and eventually building his own company, Straight Path. One moment that stood out was when he left a comfortable job to take a junior DBA role so he could grow faster, even though it meant upsetting a mentor who had supported him. Later, starting his consulting firm—and eventually hiring employees—raised the stakes even higher. What was interesting to me is how Mike frames risk as something that evolves. At first it’s about your own career, but once you build a business and people depend on you, the calculus changes completely.

T-SQL Tuesday #196: My Boldest Career Moves by Deepthi Goguri

Deepthi shared a deeply personal story about the biggest career risk she ever took: changing professions entirely. In her post, she explains that she originally trained and worked as a pharmacist, but eventually made the difficult decision to leave that field and move into computer technology. That meant starting over in a completely different industry, learning new skills, and stepping into a world that was unfamiliar and uncertain. What stood out to me is how she describes making the change even when it felt uncomfortable, because she believed it was the right move for her future. That kind of pivot takes real courage. Sometimes the biggest career risk isn’t changing jobs—it’s changing careers entirely. Much respect to her for writing an emotional blog – and admitting she is an introvert, which I am too 🙂

T-SQL Tuesday #196: Taking Risks by Steve Jones

Steve shared a story that captures what a real career risk feels like in the moment. In his post, he describes leaving a stable corporate role—where he was doing well and had been promoted—to work full-time on SQL Server Central, a side project he had been building with others. It meant taking a pay cut and walking away from the security of a traditional job, with real concerns about whether his skills would stagnate or if he could return to the workforce later. What stood out to me is how he describes it as a calculated risk that still felt scary at the time. Looking back, it worked out. But in the moment, it didn’t feel safe at all—and that’s usually how you know it’s a real risk.

Final thoughts

So there you are—some really great insights from across the community.

I’ll close with one more reflection from my own career. The biggest way risk has helped me over the years is pretty simple: changing jobs. Over the course of my career, I’ve worked for 26 companies and held about 40 roles. Part of that is because I get bored easily—especially when I’m not learning something new. When the learning stops, I start looking around.

Every move carried some risk. New company. New people. Sometimes a new technology or even a completely new direction. But those moves paid off in ways that went beyond just experience. The result has been a dramatic increase in my salary over time while still having fun in nearly every role. When I look back at my first job as a computer systems administrator making $5.50 an hour, it’s pretty amazing to see how far things have come.

And I have no doubt about this: if I had avoided risks and stayed in the same roles for long stretches, I would probably be making less than half of what I earn today. Let’s face it—money isn’t everything. But having more financial security absolutely helps when it comes to supporting your family and creating opportunities for them.

Of course, not every risk worked out. I’ve taken jobs that turned out to be bad fits, and I’ve also passed on opportunities that would have been incredibly lucrative. One that still stands out was a pre-IPO company I didn’t join—while a colleague who did take the job retired early. But those experiences taught me something valuable and helped me make better decisions the next time. And in the end, if I would have retired early, I would not have written my book Deciphering Data Architectures: Choosing Between a Modern Data Warehouse, Data Fabric, Data Lakehouse, and Data Mesh (See what I did there? Had to sneak that plug in somehow). 

The key lesson for me is that the goal isn’t to avoid failure. The goal is to learn from it and keep moving forward. I never stopped taking risks after those setbacks, and over time those risks paid off. It’s just something to keep in mind the next time you’re deciding whether to take that leap.