Dear Boss,
I’m wondering if what I’m feeling about my resignation is normal, and how I can best position myself to still start my new role with confidence despite my fears.
I gave notice at my job last week. My company is extremely small for our industry compared to the one I am going to (think: tech start-up versus Apple). I did really well in the role, and my boss’s feedback became increasingly geared toward my taking her job in the future. But I was miserable for much of my time there. Our workload was immense, and there was constant pressure to be perfect, particularly because I worked with our company owners every day. I always doubted myself , even when I was told I was doing great, because it was so easy to make mistakes (especially as my boss isn’t the most effective manager, which is another letter entirely). Every other member of my team was either on a performance-improvement plan, just off of one, or fired for poor performance. It felt like being a living wife of Henry VIII; I never knew if it was skill or luck that saved my head.
At the new job I accepted, I’ll be working on more complex projects and have more flexibility, better internal standards, and a much higher salary. Of course, I knew there would be potential downsides, too. I will be one of many on a huge team (which I wanted after my most recent experience), and working for a large public company comes with higher risks than my small but stable employer. I’ll be starting from scratch building relationships with colleagues who live both locally and abroad. It is a big step, but I thought that I had weighed every pro and con before reaching my decision.
But now that I’m in my notice period, I feel like I’m always ten seconds away from calling my boss and saying, “Never mind! I want to stay!” I know at least some of this comes from nerves over making a big change, and I still suffer from a lot of the self-doubt that characterized my time in my current role. But some of it has to do with what has happened since I gave my notice:
1. My boss has begun making offhand comments that make me doubt my decision like, “I would never work for a company that big,” “You should know we’ll be going into a second Great Depression, so layoffs are coming,” and “You were my choice to replace me, so I guess I’ll be sticking around for a while.”
2. I received a heartfelt email from our company owner explaining that she didn’t want to lose me. We also had a call where she shared the downsides of working for companies like the one I am going to and the perks of working for a small organization that “takes care of their people.” She said that my departure was an “unfathomable” loss for the company and that I should call her directly if I want to come back at any point.
3. My old employer made me a counteroffer for about half the salary increase I’m getting in my new role, along with some other perks. While this was tempting, given the conversations above, I opted not to accept because I couldn’t say for sure I wouldn’t want to leave again in a couple of months, and I’d rather keep this bridge intact than burn it by quitting a second time later on.
There are other reasons for my nerves. I’m seeing articles about regrets over the Great Resignation, boomerang employees, etc. On top of the many great reviews of my new company, there are bad ones. And I’ll miss the colleagues, work, and opportunities at my old job.
At this stage, my decision is final, and there isn’t really any point to agonizing over it any more. So why am I? And how can I move past it so I’m not carrying this worry into my new job with me?
It’s so, so normal to second-guess your decision to leave a job. Of all the things people write me, “Should I quit my job?” is the single most common. “I feel too guilty to quit my job” is the second most common. (And just as an interesting point of trivia, the next most common is “I want to tell someone to stop doing X, but I’m afraid of making things awkward.”)
Even without the comments your boss and the company owner have been making, it wouldn’t be surprising for you to second-guess your decision. When you’ve been working somewhere for a while, it becomes comfortable. Even when you have good reasons to quit, it’s nerve-wracking to leave a situation where you know everyone, they know you, and you’ve learned how to get things done in a specific environment. Most people have anxiety about starting a new position: You can’t be sure exactly what kind of culture or team you’re walking into, you’ll have to establish your reputation all over again, and the details of the work may be unfamiliar. It’s legitimately unnerving.
Then throw in the commentary you’re hearing from your boss and the company owner, and it’s no wonder you’re questioning yourself. Those remarks, by the way, might not be purposely designed to undermine your confidence in your decision — but they sure sound like it. What exactly is your boss’s goal in saying things like “I would never work for a company that big” and “I guess I’ll have to stick around now,” if not to make you worry and feel guilty? Please see those for what they are: Your boss flailing at losing you and possibly lashing out as a result. Don’t give credence to input that clearly isn’t coming from a constructive place. (You mentioned that your boss isn’t a good manager, and it’s really showing here.)
As for the company owner’s regrets at not keeping you … well, if it’s such an “unfathomable loss” for the organization, the time for it to offer you a higher salary and other perks was before it had already lost you. If she was able to offer you that raise once you were leaving, she was able to offer it to you earlier, too; she just chose not to because she didn’t think she needed to. She’s trying to dress that up as flattery and appreciation now, but the timing speaks for itself.
The thing to remember is this: You started looking at other jobs for a reason. That reason is what’s driving that voice in your head now, telling you not to accept your company’s counteroffer. Because, as you say, you might want to leave again in a few months. You were miserable for much of your time in this job! Your workload was overwhelming, the pressure to be perfect was unrealistic, your manager was incompetent, and literally every other member of your team was fired or threatened with being fired (leading, no doubt, to your own job always feeling precarious as well).
You’ve traded all that for better work, more flexibility, and higher pay. And yes, there inevitably will be downsides you haven’t foreseen, because that happens with all jobs. But you carefully weighed the pros and cons and made what sounds like a smart decision based on all the information available. Don’t let a combination of very normal nerves and management undermining you make you doubt yourself now.
Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email [email protected]. Her advice column appears here every other Tuesday.