Knowing When It's Time

Sometimes you have to move along and knowing when is pretty simple

It’s Time

There comes a time in (almost) everyone’s career at a given company where you finally pick up your head, look around, and wonder “what am I doing here?” That’s normal. You should have that feeling every once in a while. It serves as a nice check in to make sure you’re still on track and doing what you should in terms of career and, in many ways, life.

And in that moment where you pick your head up and with the full clarity that rare moment provides, you need to ask yourself whether or not it’s time to move on. That recently happened to me and is what prompted me to start this blog you’re reading right now.

After 6 years starting with Roadtrippers and moving through a couple of acquisitions and consolidations to form Roadpass, last Friday was my last day. It was hard to move on from the amazing people with whom I’ve shared a ton of ups and downs and, fortunately, a lot more wins than losses. They’ll do great and I’m excited to see it.

(PS: for those who care, I’ll post again soon with more info on what I’m considering next.)

But enough about me, let’s get into it. Given this big change for me, it’s a perfect time to share what I’ve figured out over the years about knowing when it’s time to move on from your current job. First off, let’s all agree that making this decision is by no means easy and I'feel very fortunate that I even have the option to walk away from a nice, secure job to find something new. I get that not everyone can do this, but that doesn’t mean you’re stuck forever in a role that’s just not a fit anymore. Start looking now if you see that a lot of what I’ll share below is true for you.

How will I know?

It comes down to four possible reasons when you should recognize it’s time to start looking or just walk out the door. Note that I’m not including the case where you’re unfairly paid or mistreated by managers or colleagues. Those are obvious. Get out now. It won’t get better. Fortunately, I’ve never really experienced this, so we won’t focus on that here.

1. The company has grown up

This happens when you start at a small company and it starts doing well (hopefully, thanks to your contributions). What you’ll notice is that your role, which seemed to have a tremendous impact on whether the company succeeded or failed, no longer has quite the same impact. This is normal and healthy. You’ll notice your job getting divided up among more and more people who ideally are better at those tasks they’re taking from you and who have a lot more time to focus just on those tasks. You should welcome this; it’s a sign the company is growing and specializing. This is (almost) always a good thing for the future of the company.

BUT…it might not be good for you. You might love doing lots of different things and being “the guy” that owns a ton of different things. You might really relish being in a place where your absence is obvious and big things would break if you stopped showing up. The bad news for you is that your company will never go back to that once it’s moved on. So, if you genuinely love the type of role where you’re doing everything, you probably need to find a different place to do it.

2. Not adding value

This one is related to the previous item, but has an important nuance that very few people ever recognize. I learned this one when I was a pharma sales manager. I had a very experienced sales rep working for me who had previously been a manager for many years and decided he no longer wanted to manage people. He was easily my best sales rep (unlike what you might have expected from someone taking a voluntary step back). He was doing the opposite of phoning it in. I was glad to have him on the team. He was one of those team members you never had to worry about and who you genuinely enjoyed working with (in my case, that was spending an entire day in the same car making sales calls, so you’d better like these people).

And then one day it was over. He came to me and said he was resigning. He wasn’t taking another job for a fat raise at some other pharma company. He was quitting because he no longer felt it was fair to the company. That is, in his mind, the company was longer getting a reasonable return on the investment they were making in him. And that was a pretty big investment between salary and benefits, bonuses, and a company car (among other thing). But being a pharma sales rep was definitely changing; it was becoming nearly impossible to meet with physicians, which was the entire point of this job. (Side note: I still have no idea how “pharma sales rep” is still a job today. Maybe I’ll write about that at some point.).

This is obviously a very high integrity move that a lot of people might think in their head, but don’t do anything about it. There’s the aspect about not wanting to “take advantage” of the company, but this was a giant pharmaceutical company; they could spare the cash. There’s an important additional aspect here and that’s feeling that you’re actually making a difference; that you showing up every day actually matters. And in the case of this sales rep, that’s what was really bugging him. He couldn’t make a difference anymore and that feels horrible. It’s hard to just point you car away from your house for 8 hours in these cases.

3. Sunday Dread

While I hope that you’ve never had this feeling before, you probably have had it at least a handful of times. You know the feeling. It’s eight o’clock at night on a Sunday and your mind suddenly remembers that you have to go back to “that place” again tomorrow. I call that “Sunday Dread.” It’s that feeling of dread of having to go back to work tomorrow.

I’ll make simple…if you have this feeling on most Sundays, it’s time for a new job. This situation ruins 50% of your weekend and probably a bunch of other time since you’re probably feeling it each and every evening. Without citing a ton of research, I can tell you that this is terrible for your mental health and poor mental health is literally shortening your life while making every day a struggle. Please move on. There is something better out there. And yes, something better that pays slightly less is 100% worth it. Consider the amount you’re forgoing in salary as a fee to be happy. How much would you pay for that right now?

4. Strategic Disagreement

The final one on my list is a straightforward one as well. For whatever reason, it could be a change in leadership, a new investor, or new direction from “the market,” your company is headed in a different direction strategically. Like many changes, this often can be something positive. It might be a change you disagree with. And, it might be positive AND you might disagree with it. They aren’t mutually exclusive.

Of course, you’re not always going to agree with everything your company does and you might not be in the position to shift the things you disagree with. That’s the agreement you have with your company: they send you money and you go along (generally) with what they say. The only way around this agreement is to work for yourself (PS: and make sure you don’t have investors because if you do, you don’t work for yourself).

So, I’m not suggesting to quit the minute you disagree with something your company is doing (unless it’s illegal or immoral somehow…that’s a different story). But I am suggesting that if the company is pursing a strategy you just don’t agree with and can’t see a path forward to where you might be sold on this new strategy, it’s time to move on. The reason for this is simple: you absolutely will be frustrated more often than not. And that will lead to an acute and chronic case of item three above: Sunday Dread. You will be constantly swimming against the tide and working on things you don’t believe in. But if the company is fully committed to this new direction, you’re very unlikely as an individual contributor to change the company’s direction and momentum. The choice you have to make is whether or not you can get on board. If you can, great. Throw yourself into the new strategy and how you can help deliver on the goals aligned with it. If you can’t, it’s time.

The End…ish.

That’s the list.

For those who know me, you might be asking, “which one is the reason you decided to move on from your last role at Roadtrippers/Roadpass?” It was mostly reason number one (“The company has grown up”) in my case. We brought on a ton of talented people who have all stepped up and allowed me to hand off one responsibility after another. At the same time, many of these folks have improved upon processes or ideas I previous managed (which is exactly what you want), so I came to a simple realization that they don’t need me anymore. As a leader, it’s really what you want to happen even if it means you need to go off and do something else…and here we are.

Jonathan Richman (your friendly author) has spent more than 25 years learning hard lessons about business (and life) across multiple industries and all sorts of different roles. His latest endeavor is a new full-service automation agency, Obvify.

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