How Does Career History Shape Your Work?

The linear path is not always best

Over the past 15 years, I have worked in hospitality, retail, tech, and agencies. In these industries, I have held over 10 different titles. Recently, I have been thinking about my career history and how it has shaped me into the consultant I am today.

Currently, I am an Operations Consultant. Looking back at the last 15 years, most wouldn't see how I got here, but I can see it. The through line for all the roles I've had was that I have always been operations. From retail employee to head of product management, I have always helped the business run behind the scenes. So when I jumped ship from my 9 to 5 in 2021, it kind of just happened.

More broadly speaking, how did my experience as a server play a role in my career now? What about retail? More directly, how did QA, design, and product?

As a server, I learned the fundamentals of hospitality. I learned how to listen, work under pressure, deal with work conflicts on the fly, and even remember long and complicated orders without writing them down (yeah, I was one of those servers). The biggest thing I learned was adapting, constantly. I was the type of server that was cross-trained. I would serve one moment, seat tables the next, hop behind the bar for a few, and even jump into the kitchen.

I worked two very different types of retail jobs: commission-based and pure hospitality. I am a shit salesperson, so I didn't love the commission-based job at all, but I thrived at hospitality. As someone that has always been tech-minded—working at Apple, with my restaurant experience, worked well. I was able to empathize with customers, understand their technical requests, troubleshoot at a high level, and build solutions to meet their needs.

Once moving into tech, more directly, being a QA engineer, designer, and product manager just clicked. It took a few months to get up to par, but the foundations built on restaurants and retail set me up for success and allowed me to stand out. Most people I worked with came from a 4-year college, understanding all the technical processes, while I did not. Sure, I was technical, but I didn't code or write scripts. I aligned with the user, the people using the products above all.

Now, 20+ years after starting my job adventure, I am an operations consultant. Yes, I thrive in building systems, but what is more important are the skills that I picked up along the way. I am cross-trained, empathetic, understanding, and can build and troubleshoot systems.

I mention this story because sometimes I look back at this strange path that I took, wishing that I just went the linear route. I could have gone to the 4-year university, gotten an internship, moved into a full-time role, and bounced between big-name company x to company y. That way might have gotten me into debt with financial aid, but I would have had a more cemented future.

But then I remember that the journey is more important than the destination. While I am not making senior Software Engineer salary, I do well enough. Sure, my clients don't think about how my unconventional background benefits our projects, but it does.

As consultants, we have discovery calls, pitch ideas, send proposals, and wait for a decision. During this time clients generally interview other consultants, some that I know. Usually, they have a traditional background, a flashy degree, or a large team behind them. But, often enough, this one-man show with minimal college wins the project. Looking back at those deals, it's not the technical skills or system-building mindset—it's the skills I learned as a server, retail employee, and entry-level QA engineer.

So when you look back at your career, try not to regret every odd job or speed bump that you had to go over to get here. While some careers are linear and predictable, the ones that aren't are more resilient and adaptable. All jobs, regardless of the title, shape the way you work today.