Editor’s Note: I get the same sort of email a lot lately – from friends and folks in my network – and there seems to be a common thread. I thought I’d address “career stagnation” in this post.
So you’re there at the job, and you’re just not feeling it. Maybe it’s not what you signed up for, maybe you’re looking around and seeing that people are doing less and getting paid more. Maybe the boss, or the boss’s boss, isn’t quite management material. (You know that most people leave because of a bad manager, not because of money…right?) Or maybe the company itself is built on a house of cards and the collapse is coming soon. (If you are anywhere near startups, you know all about this danse macabre.)
You could be new at this job, new at this line of work, or a grizzled veteran. The company could be old school or a startup or something in between.
For you, wayward career person, we present this post: What to do when the wind is out of your career sails.
Five Steps to Freedom. Or to a New You. Or Something.

1. Don’t Panic.
The first, and perhaps most critical step, is to look around, do some soul-searching, and find out whether or not this is a short-term problem. It may very well be: my first big city professional gig looked like a nightmare on paper after a couple weeks. And then it settled down – I was able to take on all sorts of responsibilities mostly because we had (1) no budget and (2) no resources. So I did just about everything.
After six months, with “busy season” in my rear view mirror, I realized what the job really entailed, and what the career prospects were for me. It was a matter of getting another year under my belt and then having a burnished resume and the chance to go elsewhere – something I did right at the two-year mark.
My suggestion to you is to ask around – truly ask around – and start to build relationships with people in other departments or at peer companies. After doing your due diligence, you might realize that it’s NOT that crazy, and you just need to dig in and focus on making an impact.
If that’s the case – this is a short-term problem and you’ll eventually be just fine – congratulations! Skip to the bottom of this post.
If it’s not the case and you are in for more pain at the office than you want to subject yourself to, it’s time to move on to step two.
2. Ask for More Clarity.
Best to use a “ripped from the headlines” example from my buddy “Mark,” who shares this story.
The background: a small department, a couple young people in that department, and our friend “Betsy” was the one who wasn’t feeling it. The reason she wasn’t feeling it (and I was the manager so I saw this first-hand) was pretty simple. Of the four people in the department who reported into me as a manager, Betsy was the only one who could be called “rock star.” The other three varied in skill levels from “okay” to “above-average,” but none of them could hold a candle to Betsy.
The clincher for her was realizing that she was grossly underpaid. Of the four on the team, she performed the best and made the least. And it sadly wasn’t even close – there was about a 15% gap in salary.
She came to me with two requests, and I thought those were rather savvy (especially given her age and the fact she was a “Millennial” and, therefore, was supposed to be whiny and stereotypical). Request one: What can we do to address the salary inequity? I didn’t want to lose her, so I made a promise to “get right on that” – requiring a difficult conversation with my own manager, who controlled the purse strings. Request two: What can we do to forge a career path for the four of us in the department? This, too, became a priority for me – and it became much easier for me, the manager, to have a chat with my boss if I wasn’t just asking for more money for one of my people.
Mark reports back with the bad news (for his company): after a few months, nothing had been done to address either request. The company dragged its feet and, while Betsy kept performing at the highest level, Mark realized that she was going to head for the hills soon.
Remember the first step – Don’t Panic? Well, if you follow the process at your organization and you raise the right flags, pretty soon the true colors will show for your employer. You can ask for more clarity – and that doesn’t have to mean a request for more money – but you may not get more clarity. If you’re not panicking throughout this process, there’s a chance that you might want to work on Step 3 – and do so at the same time you’re looking for clarity.
3. Activate Your Network. NOW.
Networking is such a pain, right?
Well, it depends how you go about it. Another example, this one from my pal “Jackie”…
After seven years at my company, I had maxed out. Not only that, I was staring the same-old, same-old in the face and could pull the binder off of the shelf and just do the same thing over and over. It got boring and I was ready for a shift.
I also got at least a little scared because I realized I didn’t really have an active network. So I started building one, a little at a time.
It started several months before my desired departure date. First, instead of applying to every company under the sun, I asked around and tried to find friends who had friends at target companies. Then, I’d ask to sit down for coffee with the hopes of making it less of a “win-win” and more of a “win-lose.” [EDITOR’S NOTE: Learn more about the “win-lose” by reading one of the few books I recommend.]
For example, I have a relative who has been friends with someone at a target company for years – and it turns out this person worked in the department that would interface the most with the new hire that I wanted to become. Instead of just saying “can I meet this gentleman?” I crafted an email that my relative could send to the guy, and it was all about the research that my current company had that could help this guy make the most out of working with the new hire, whomever it ended up being.
So we met for coffee and that opened another door and another door and…
A few months later, Jackie did land her dream gig – same industry, different place, renewed focus.

I’ll be honest: networking is actually pretty bogus if you just look at it as “sales.” But if you look at it as a “win-lose” – they win, you lose – you’re going to have a much better time of it. And you’re going to find yourself opening doors right and left. And you might make some friends along the way.
4. Introduce Yourself to the “Side Hustle.”
I’ll take the mic for this one: I decided several years ago to grab a side gig as a wine salesman. I loved the people I worked with, I loved the product, and I loved interacting with customers on the sales floor.
Was it easy money? No. Did I get rich at it? No.
Did I learn a lot about wine? Customer service? The Four Ps of Marketing? Etc., etc.? Absolutely.
You don’t have to sell wine, of course. You might have any number of skills or interests that can be turned into a side project that will keep you engaged for a few hours on the weekend or for a couple nights a week.
It’s called a “side hustle,” not a “new job,” for a reason. Sure, times may get lean and you’ll want to have the opportunity to pick up more hours – and a side hustle is great for that. But the main goal here is a breather from that day job – the one where, you remember, the wind is out of your sails.
5. Learn to Thrive in Ambiguity.
Honestly, some people are great at this and others walk around, as an old CEO I used to work for would say, “going from desk to desk, looking for somewhere to plug in their umbilical cord.” His point: not every job will be crystal-clear in its role, responsibility, and job description.
If you have to start your day with a clear picture of how you will spend every single minute, and you’re not prepared to roll with the punches, then you might need a couple lessons in randomness.
If you’re the one who loves randomness – and, honestly, that’s how I roll – then look at this as an opportunity to choose your own adventure.
I’ve worked with people in ambiguous environments who use that to their advantage: knowing that the boss won’t be asking for updates every thirty seconds means you can be strategic in what you do, and even more strategic in how you report on what you do.
Example: you’re supposed to create an agenda for and host a monthly conference call that was the idea of someone who left the company a year ago. For some reason, these conference calls still take place monthly – and they’re not well-attended and no information is really shared. Plus, the big boss doesn’t really concern himself with the fact that the calls are taking place, as he just wants to know whether the work is being done.
So you cancel the conference call, and you reach out to the attendees via email, offering to chat one-on-one about things that they need help with. Some people will ignore you, some might call you directly. Some won’t even care. Others will celebrate the fact they got one hour a month back.
It’s a win: but if you’re a rule-follower, you might have to start looking for rules to break.
Remember, your goal is freedom. Freedom might be coming from the job you don’t like anymore – but it also might come from enjoying your time while you work on the exit strategy.
Tried all that, now what?
Are you sure? Super-extra sure?
Probably time for Step 5A: Positive frame of mind.
I say this from experience, having spent more than enough time as a freelancer, free agent, and entrepreneur: The right “thing” IS out there. It helps big time to have the right attitude. Doesn’t work out this time? Move on, go after it next time.