How to Leave a Successful Career

The key to leaving a job you're good at or one that pays well is to understand what’s keeping you there.

Some of you are reading this and wondering why someone would quit a job where they're killin' it or leave a position they enjoy. Well, sometimes we get this sense there’s more to life than our “successful” work positions.

Quitting a comfortable career where you may be excelling doesn’t sound logical and, honestly, many people don’t get it (although you may be surprised by how many people will secretly cheer you on).

That’s what happened with me. I quit my job and when I told my colleagues I was leaving, many of them whispered how happy they were for me, or how they wished they had the courage to leave.

I enjoyed my job. I was making a decent living working at a consulting firm with clients from Fortune 500 companies. My department helped them execute and communicate changes within their organizations.

I liked managing multiple projects, interacting with clients, working remotely sometimes and collaborating with super smart colleagues.

What eventually became apparent, though, was how working in a fast-paced, high-intensity environment with the demands of clients and directors wasn’t going to be sustainable for me. I was doing the job well, but it wasn’t worth it.

The expectations of the job required missing out on life. The salary afforded vacations but you could be shamed for taking time off or, through nonverbal cues, expected to work on days off.

I recall working at the doctor's office in a paper gown right before getting a biopsy (the results came back benign). At some point, I remembered this wasn’t normal. I’d forgotten habitually skipping bathroom breaks and lunch wasn’t OK.

I realized having chest pains, hives and issues sleeping weren’t things I should continue ignoring.

So back to what I was saying about the key to leaving a job you enjoy, or one that allows you to make a good living. I know firsthand it can be tough, but it may be time to consider living a more fulfilling life based on purpose and not paychecks.

Here’s how you do it:

Really think about why you’re staying. Here’s common reasons I hear, or that I can relate to personally: the money, stability, lack of support, or fear of failing, having regret, the unknown or what people would think.

It’s easier to stay. It’s like when you’re in a relationship you know you need to end but you can’t seem to leave. It's comfortable. It's familiar. The person may have become a part of your identity.

Leaving a job that’s rewarding, paying good money or offering stability is hard, especially if you grew up with parents like mine who still look at me sideways when I talk about passion and purpose. Their focus is getting benefits and being able to pay bills — period.

The common aforementioned reasons for staying are a good starting point, but force yourself to dig deeper. For me, I tied my self-worth directly to my work ethic, which resulted in “accomplishments.” These accomplishments manifested into tangible things like money, job titles, cars, homes and vacations that people noticed.

I also realized my addiction to work. I couldn’t stop working. My job only fed my inner craving to work like a madwoman. I had no idea I was getting a high from work. This epiphany was huge.

What’s really keeping you at your job? Why are you afraid of instability, what people will think, making less money or sticking to a profession because if you left you'd still be paying for the degree that got you the job in the first place?

You may work really hard to pay bills, and paying bills and buying things equates to stability and "normalcy" and that may be because you didn't feel like you fit in when you were younger, or perhaps from some trauma like bullying or abuse.

Getting to the root of what’s keeping you there leads to making a decision for a critical question. Is it worth it? You may find it is for now, and that’s OK. You may decide to never switch careers or start a business, and that’s OK too. The idea of doing this exercise may even be daunting.

If you need support with it, sign up for a free 45-minute breakthrough call. Or, if you’re ready to explore your why because you don’t want to look back at your retirement thinking, what if, let's chat.

It can be hard having an epiphany on your own without a catalyst for self-reflection. Or, it may be challenging taking this first step of exploring your personal why of what you’re holding on to and why you can't seem to let it go.

My role isn’t to convince you to leave your job. It’s about exploring what may be holding you back or discovering what you’re supposed to do while here on this earth.

One day you may decide you’re ready to move your life in another direction and, when you do, you’ll know where you’re going. Or, you may be ready to make moves now and need help figuring out how to transition.