8 Things Paul Simon Can Teach You About Leaving Your Job

iStock_000004110912XSmall “‘The problem is all inside your head’, she said to me. The answer is easy if you take it logically. I’d like to help you in your struggle to be free. There must be 50 ways to leave your lover. “

Just like Paul Simon’s lover, some jobs need to be left, and fast. 

But as she says, the problem is in your head.

It can be hard to know when leaving your job is right, because we tend to take very seriously things like a paycheck or health insurance. And that internal struggle can lead to confusion and paralysis, just like it did for poor old Paul. 

So, how can you know if you really should start planning to leave your job? Here are 8 questions to ask yourself: 

1. Can I manage financially? Sometimes making a job or career move can, at least initially, impact your bottom line. Before doing anything, you should be sure you can manage financially and also account for things like health insurance benefits. Remember that you may never earn as much from that next thing as you do from your job today. But there still may be a magic number that you can live with provided that you get to enjoy your work. 

2. How much is this costing me psychically? Sometimes it’s too brutal to think about going back to work. If your job sucking your soul, leaving you depressed, anxious, and traumatized, you may place a very high value on the idea of leaving, no matter your answers to the other questions. Like an abusive relationship, sometimes getting out is just the right thing to do, no matter what pieces you have to pick up later. 

3. How clear am I on what’s next? Your next relationship won’t be perfect, and neither will your new job. You’ll want to create not only the vision of what you want next, but you’ll also have to take an  honest look at what that next thing will be like. It can be easy to feel that the grass will be perfectly green once you’re out of your terrible job and onto something else, but that’s not always true. Take the time to account for your strengths and weaknesses, know what tasks you’ll love and what will be hard, and overall have a realistic view of your goal. 

4. Is my family in support of me making a move? It’s like bringing someone home for the first time to meet your folks. If you have people in your life that are important to you, you’ll certainly want to include them in this huge decision. Their input may not determine your final choice, but it may influence how you go about doing what you want to do. In addition, they’ll be very glad you included them. 

5. What are you leaving behind? Be really clear about what you’re leaving when you decide to move on from your job or current career track. It might be a decent paycheck, but it could also be other benefits as well such as unparalleled training or a chance at advancement that might not exist elsewhere. Like your old boyfriend, you might not want to regret leaving a (mostly) good thing. 

6. What do you really want? Just as it might be tempting to fantasize about how a new relationship will be better, you might believe finding a new job is the solution. But sometimes a complete overhaul isn’t needed. Ask yourself, are you thinking of leaving your job or career because it’s not the right fit for you, or because you feel undervalued? If what you really want is to do your same job in a better environment, or a chance at a promotion, the ability to work on certain types of projects, etc. you may not have to leave your current job to get that. By being very aware of what you’re truly after, you may save yourself a lot of work.  

7. Is there a comfortable transition? I’m not suggesting you have an affair exactly – well, ok, I guess I am. Is there a way that you can gain skills, experience, or credentials you’ll need for your new position before you give up the comfort of your paycheck? 

8. Is your passion outside of work? Maybe you don’t love your job, but it affords you the lifestyle to do something that you do love – something you might not otherwise be able to pay for. I love to see what we can create by engaging in our passions. It’s only when you tap into that energy reserve of passion that you can reach for true excellence. But sometimes, this is just something that happens outside our jobs. Sometimes, even, getting paid to do it ruins the experience. So if you’re more or less content to do your job and to pursue your passion as a hobby, don’t feel you have to make a living off your passions if that doesn’t feel right. 

In the end, the decision to just leave (or not) will be much easier if you get very clear on what’s keeping you there and what’s urging you to move on, and if you understand the consequences of each choice.

And just like Paul, once you start to see the possibilities and choices that exist you’ll feel much better.

What’s keeping you stuck or encouraging you to think about leaving your job? 


Career Building, Career Change, Success

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