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Q&A: I am miserable at my job. How do I know when I can leave?

Hey, everyone! It’s Doug. I know Heather already wished you a Happy New Year last week, but I might as well say it before we’re cut off. Happy New Year! I am excited to be answering all your questions here in 2024. Let’s do this.


I work a million hours a week as an attorney, and I am absolutely miserable at my firm. My husband wants me to be happy, but our family has grown accustomed to a certain lifestyle, and I know making a change will result in a pay cut. How do I know when it's the right time to make a move?


Before I launched my own wealth management firm, I worked for several different financial advisors. I’m very grateful for the opportunities they gave me, but despite our best efforts, each of these relationships ended...not great. I was so miserable in the months leading up to my eventual departure. Those periods of deteriorating morale took such a toll on me and every aspect of my life. Heather was there. She can tell you.

As humans, we easily grow accustomed to people, places, and of most of all, incentives. They convince us to adopt the “devil you know is better than the devil you don’t” philosophy. We also love to be comfortable when it comes to our careers and how we make our money. I see it with my clients all the time. They, like you, find it incredibly hard to leave a well-paying job they’ve been at for a while. But most of the time, they reach a point where they can’t take it anymore, and a change has to be made.

You should have a plan before you do anything that impacts your income. You’d think this goes without saying, but I’ve seen people quit in a fit of rage under the assumption they’d make quick work of the job market and be sorely mistaken. Even if your skills are very marketable, the interview process takes time, and there’s always a risk that internal bureaucracy might slow things down. 

Also, you’re a lawyer. Do you have a transportable book of client business? Are you just looking for new colleagues to work with, or are you planning to leave private practice behind altogether? As I’ve observed with Heather’s transition into in-house work, the responsibilities are quite different. While you’re still employed, DYOR (that’s “do your own research”). Set up some meetings with former colleagues who sit in the roles you might be interested in. I know lawyers work in demanding environments and it’s hard to shift your priorities, but if you know you want to leave, make a conscious effort to prioritize as much as possible the due diligence around your next career move while you’re still employed. You’ll thank yourself later.  

Now is also time to dive deep into your household finances with your husband. Calculate how much you need every month to maintain your current lifestyle. You need to know what's being spent so you know exactly how much income you’ll need in your next role to avoid having to make any lifestyle changes. You may not be able to maintain that lifestyle, but by understanding how much it costs, you’ll know what kind of adjustments have to be made if you’re bringing in a smaller paycheck. 

If you do feel you need to maintain your current lifestyle, you can fill in the income gap with your cash savings. But consider this more of a Band-Aid than a fix. In your new prospective role, how quickly can you increase your income to make up the difference? Is there a bonus structure that might take care of it at year-end? What do raises look like?

While you’re still investigating these things (and gainfully employed), you might want to alleviate some anxiety by redirecting your long-term investments into savings to have more cash on hand for the move. 

Above all, communicate with your family. Explain how you’re feeling. Tell them you’re reaching the end of your rope and need to leave. Even if you feel like you’re letting them down, they need to understand and hear it from you. I bet if you’re open about where you are at, they will view your health and happiness as the most important priority.

Remember, there are feelings and there are numbers. Use the numbers to retain control over these tough conversations. Methodically planning your departure - and including your partner in the process - will make this feel like a team strategy with a team solution.

Change is hard. It’s uncomfortable, especially when you’re settled. But sometimes, you have to embrace discomfort to improve your life. By getting organized, providing yourself with a margin of safety, and communicating with your family, you can make this move. You deserve to be happy, and that’s the bottom line.  

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The content shared in The Joint Account does not constitute financial, legal, or any other professional advice. Readers should consult with their respective professionals for specific advice tailored to their situation.