Kassidi Stynnett
October 19, 2023

Role With It

The reality of working for a company in 2023 is that there is very little incentive to stay longer than three to five years at the maximum; especially in tech. Life and workplace politics for Millennials (1981-1996) and GenZ (1997 – 2012) aren’t quite the same as when GenX (1965- 1980) or Boomers (1946 -1964) were climbing the ladders, in quite literally every industry.

Here’s why:

  1. All companies are unable to keep up with inflation (the highest price of gas I just saw in Los Angeles last week was $6.75 and it’s already gone up 10 cents as of this week).
  2. Staying at a company for any amount of time now does not guarantee a promotion or monetary increase, additionally most pensions do not exist anymore.
  3. Most working folks [in tech] can stay at a job for 6 months to a year and switch companies for a monetary increase or go back to a previous role with a compensation match.
  4. GenX seems to wind up on the executive leadership teams at these [tech] companies and appear to have more of an open mind about workplace innovation; however, when things get challenging, they seem to default to the antiquated workplace mentality of “hard work pays off” and “respect your elders”. Rather than taking a knee and giving someone coming up under them a chance, listening or implementing newer practices or initiatives proposed by perhaps Millennials or GenZ, who grew up on “work smarter, not harder” they simply steam roll their needs across the board.
  5. Everyone is burnt out, beyond repair; but that doesn’t void our bills or our responsibilities; therefore, I do feel like we keep searching for the next high and what doesn’t give a dopamine rush like a new job with a potentially new salary?

I could probably list 30 reasons why there’s no incentive to stay put, but even with the ability to switch jobs every few years, there’s a substantial amount of constant adjustment and pivoting that comes with it. It’s like starting school for the first time. Maybe we don’t remember day one of kindergarten vividly, but I’m sure we remember wanting to make friends and that we were safe. 

No company on earth has it all. If they have a great culture, perhaps the compensation is under market. If they have great benefits, perhaps they contribute pennies to their company match. If they seem to have it all, perhaps there’s zero real career progression. 

In the last seven years, I’ve worked for three start-ups. The first one, back in 2017, laid everyone off after I had been there just shy of two and a half years. Luckily, I was able to find another role within the next three weeks and I stayed there for four years. I recently switched companies four months ago and above all I’m grateful for the road travelled. Without those first six and a half years, I wouldn’t have broken the six-figure threshold or have the hands-on experience I have today. While everyone’s journey is different, I do believe there are some psychological and professional suggestions that can help anyone’s transition from one company to another. 

Here are the ones in my top 10:

  1. Ask the hard questions when interviewing, such as “how do you think the company will be doing in the next couple of years or why did this role become available?”
  2. Communicate your needs from jump and document everything.
  3. Keep your resume updated as soon as you learn new systems, processes, and work on different projects.
  4. Remind yourself that everything is temporary, as working for anyone is never guaranteed.
  5. Align yourself with a confidante and/or mentor and learn as much as you can from them.
  6. Take advantage of the resources and benefits the company offers as soon as it becomes available to you, such as learning stipends or mental health benefits.
  7. Speak up but adhere to boundaries once you figure out the communication and implementation culture.
  8. Keep your eye out for new opportunities within the company, such as ERGs, clubs, cohorts—you never know who you may meet that can connect you to a related internal opportunity or external one.
  9. Take your PTO—if you do not feel well or need time off for anything, communicate in a timely manner with your manager and take it.
  10. Don’t give up on aligning yourself with what is going to work for you and your personal and professional situation. Be delusional until it pans out.

Change will forever be constant and staying anywhere—specifically professionally in this case—when you can’t see progression, you don’t feel valued, or you simply know you can do better are all valid reasons to seek out the next opportunity. There’s no shame in starting over as many times as you need, because you are the only one that can determine what fulfillment feels like for yourself.