Should I stay or should I go?

Thinking of making a career change?

Good luck getting “The Clash” song out of your head. This 80’s rock song strikes a chord with many in the professional world who ask the question — should I stay in this job, or is it time to go?

In late April, I had the opportunity to speak on a panel for WEST (Women Entering and Staying in Tech) on career transitions. We discussed the major changes we’ve gone through, how we mitigated risk, mentors and mentees and when to take the leap to a new job. Based on conversations I had at the panel, I realized many people had similar questions. Here are my thoughts and opinions based on my own experience.


When you feel comfortable and cushioned in your job it’s a feeling of relief. Like laying in hammock on a warm summer’s day — everything is pleasant and as it should be. But are you getting better? Are you being challenged? Is it possibly time to leave your current position or do you simply need to adjust your thought process to appreciate the flexibility you’ve been given?

Maybe it’s time to sit down and ask yourself a few questions:

  1. Over the past 6 months, what have you accomplished at work that you’re proud of?
  2. Over the past 3 months, how many times have you felt inspired by your work?
  3. Do you have a mentor or leader you look up to at your work?
  4. Do you respect your coworkers and the work they produce?
  5. Is your attitude at work mostly positive or negative?
  6. Do you find yourself with RBF (resting bitch face) or zoning out frequently in meetings?
  7. Do you sometimes daydream about punching your boss in the face?

If the answer to the above questions were mostly negative then you might want to start thinking about what you really want out of your career. Regardless of how great that hammock feels, it’s probably time to leave. Before you awkwardly roll out too fast and jump ship it’s good to consider why you feel the way you currently do and what actions you might’ve taken to get yourself into this position. I’ve had my ups and downs at work and have been able to reflect and see where things started going south — or where I just knew it was time to move on.

Making a career move can feel like jumping out of a plane

Keeping with the vacation adventure theme — I sometimes think of career transitions like skydiving for the first time. You ride on the floor of a small plane up 15,000 feet in the air not really knowing what to expect. Before you know it you’ve made the jump out into the unknown sky with nothing but a parachute to stop you from dying. The fear is real. But when it’s over and you’re back safely on land the adrenaline rush is more than you could’ve ever imagined and you wouldn’t question the opportunity to do it all over again.

The ride up

My first real job out of college was at a small software development company in Tampa, FL — let’s call it “Company A”. I was hired on as a web designer but my job responsibilities far surpassed that. Over the three and a half years I was employed there I found myself working directly with clients in a Project Manager role, preparing proposals like a Sales Representative, creating new service offerings, doing product design, building and maintaining web sites with content management systems, developing the many spin off brands for the company and its clients, maintaining social media profiles, creating marketing materials and managing junior designers. You get it.

It was a lot to take on especially at the ripe age of 21 — but it was fun! I didn’t care that it was stressful at times or that they asked me to color in a coloring book at my interview. Sure, it was absolutely ridiculous, but that was the spirit of the team. It was completely unorthodox, out of control and there was no such thing as HR in that company. I watched candidates come in for engineering interviews and get bombarded with dodgeballs. Not the most inviting way to get introduced to a company but it was a sort of right of passage to see if you’d fit in.

I really loved working there and made so many great friends during that time but at about 2 years in I started to feel the urge to move on. There were many reasons I felt this way, one of which being that my 32k salary was not proportionate to the amount of work I was doing and the value I brought to the company. Another reason was the burden of my student loans and living paycheck to paycheck for the previous two years “paying my dues” in hopes for a raise that would make staying at the company worthwhile. I did get multiple promotions and eventually was given the title of Creative Director but wasn’t fairly compensated for the work I was doing. I didn’t have a mentor and I felt I had hit a wall creatively. And yet, I stayed because I felt a sense of community and belonging with my work family.

The jump

At the 3 1/2 year mark I received a job offer that more than doubled my salary and gave me the opportunity to have a bigger impact working with thousands of clients instead of just a handful. Company B was more mature than Company A and the CEO and CMO believed in me and my talents, whereas I felt over-promised and undervalued at my current place of work.

I felt quite loyal to Company B and loved working there even more than Company A. Not only was I finally making a fair salary but I once again found a group of unique, talented and vivacious individuals that made work feel like play every day. I hit the ground running and completely rebranded the company influencing everything from business cards to large scale trade show displays to their website and SaaS membership software.

My team began with one junior designer who was a skilled graphic artist but had no experience with digital media. He was eager to learn so I passed on everything I knew about building sites and digital products from Adobe to CSS to PHP to WordPress and beyond. Our humble team of two grew to ten by the time I left 3 years later.

Back safely on land

So what happened at Company B that made me think twice about staying? There definitely was a level of comfort that I gained over the years but my performance and attitude went south when I felt I was no longer valued. Sure, I was responsible for a team of designers and for all client websites as well as our brand and marketing site and had great relationships with all other teams in the company. One day the CEO (who I realize was under a lot of pressure from the board as of late) ran into my office with a new hire in tow and announced, “This is Bill Lumbergh*, he will be your new boss.” It wasn’t the fact that a newcomer to the company was being put in a position above me — that didn’t bother me at all as it’s always good to get a fresh set of eyes and collaborate with other great designers and leaders. It was the fact that I wasn’t consulted and that all my years of dedication to the company didn’t matter. If you’re no longer valued, you have no place in that company. So you get out.

Since Company B I’ve had a few more career transitions. Company C grew my coding skills and made me get back to basics while Company D gave me the opportunity to work in a much larger organization and refined my management skills. One thing I’ve learned: you’ll never stop learning and achieving more with each transition. Change is good! For me, the opportunity to expand my skill set, cultivate different products and meet new people is crave-worthy and far outweighs the risks. If you’re happy keep doing what you’re doing. If you’re unhappy assess why. Then write that shit down and work on fixing it. Every day.

Some last words of advice:

  • Dig deeper on why you want to leave
  • Figure out if your current pay is on par with market value — check out Comparably
  • Set your goals and write down what you want from your next position
  • Leave when people like you
  • ALWAYS negotiate your compensation package
  • And most all believe in yourself and demand your worth

What’s your biggest career transition thus far? I’d love to hear your story! Comment or hit me up on Twitter or LinkedIn.

Interested in being mentored or finding a mentee? Check out WEST!


*Real name has been replaced to hide identity. Bill Lumbergh is the boss from Office Space and a good comparison to this guy.