Four Questions For When You Crave Change In Your Career (But Also Fear It). The decorative background photo shows a cup of coffee on a saucer, and an open notebook on top of a calendar and a book written in French. A pen lays across the open notebook, ready for the answers to the questions.

Four Questions For When You Crave Change In Your Career (But Also Fear It)

If you are considering leaving your job within the next six months, you’re certainly not alone. A recent survey showed that 41% of American workers are considering the same.

Of those, fully half say they’re already financially prepared to do so.

And, among those who aren’t prepared yet, fully half are willing to take on debt while they search for their next position.*

To put it casually, they’re ready to rock and roll.

Still, even with the finances are in place, many haven’t taken the leap.

And I completely understand, because that was me.

As I approached my 35th birthday, I was in year 3 of a job that took advantage of me on every level. They asked more and more of me, and offered less and less.

The dreams I'd once had mattered, and I needed to be able to say I'd tried everything. (The decorative background photo is only visible around the edges. You can see two candles and some books peeking out. The vibe is cozy and healing.)

For my birthday that year, my husband took me to a beautiful lodge tucked in the foothills of the Adirondack Mountains. One night, as we lingered at the Lodge’s restaurant, he told me in no uncertain terms that he would support me if I decided to leave that job. He’d done the math, and we’d be fine.

We were ready financially.

Yet, it took me an entire year to be ready mentally and emotionally. It was the day after my 36th birthday that I finally turned in my resignation.

In retrospect, I was holding on to pride… and to hope. The dreams I’d once had mattered, and I needed to be able to say I’d tried everything. I was afraid of telling people I’d quit without another job lined up, and even more afraid to tell them I was starting my own business.

So, if you find yourself hesitant, here are four questions to ask yourself:

1. What are your options?

I was afraid of this question at first. It felt too wide open. In a vague sense, I had hundreds of options. But in a very real sense, it felt like I had none.

In the end, it helped to think in paths, rather than specifics.

Consider this: There are a handful of paths that are generally available to anyone with a traditional corporate position…

Path 1: You could stay in your current position and pursue incremental improvements.

If you work with people you trust, and your salary is acceptable, this can be a good option. Be specific about what would need to change, and have some honest conversations.

On the other hand, if the trust is broken, or you can’t afford groceries and medical care on your salary, this may not be an option for you.

Path 2: You could apply for a different position within the same company.

There are so many things that could make a job miserable that don’t necessarily come directly from the company you work for. If you know people in your company who have similar values to yours, and they’re happy in their positions, consider applying internally. You may just need to get out of the pocket of drama created by a specific manager or department. Or, you may need a position that’s a better fit.

On the other hand, if the corporation has a toxic culture or lacks paths for growth, it may be best to eliminate this option now.

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Path 3: You could get a similar position with a different company.

If you like what you do, but not the culture of your current company, this could be a great option.

On the other hand, if the position was never a good fit, and you’ve just been hanging by a thread the whole time, changing positions or changing careers may be the better path.   

Path 4: You could change careers.

This could be the best option if you’re craving massive change, and you’re willing to start fresh. If you’re not sure what else you’d do, resources like What Color Is Your Parachute, Myers-Briggs or the Enneagram can help you explore careers that would be a good fit.

If the idea of starting over gives you heart palpitations, or it would require a lifestyle change you’re not ready for, you may want to cross this off as an option.

Path 5: You could start a business.

If you have been mulling over ideas for new businesses for a while, and you’re not afraid to go outside your comfort zone, this could be the path for you.

It probably goes without saying that owning a business isn’t for everyone! If you hate the idea of being the one in charge of everything, spending significant time marketing and selling, or the financial instability inherent in a startup, it’s “buh bye” to this idea.

Keep in mind that your job isn’t just about what you do, it’s about the infrastructure of your life.

Give some consideration to the schedule you want to keep, the role of money in your life, and your tolerance for change and ambiguity, as well as your skills and passions.

So, although someone could have any one of these options, what would you consider your best options? Does one of these paths stand out to you?

2. What are your fears?

This was another question I didn’t want to face, but which proved helpful. Our fears loom larger when we refuse to name them.

There are some common fears many of us feel in these situations. What if the new job is worse? What if I try to start a business and it fails? What if I go broke? What if people gossip about me behind my back?

It’s surprisingly helpful to be as specific as possible. What exactly might happen? Who’s reaction are you worried about? Write it all out, and see if it feels more manageable once it’s in black and white.

(If you haven’t read the blog post about the difference between insecurity and lack of confidence, it may be helpful.)

3. What would need to be true for you to feel confident and secure in your decision?

We all crave guarantees, but they don’t exist in this world. That being said, what might make a difference?

If you had enough money saved to cover six months of expenses, would you really feel better? If a specific person validated your decision, would it make a difference? If someone offered you a job out of the blue, would it be an easy yes?

It’s easy to think that if you had all of these—money saved, approval from your loved ones, and a job lined up—that it would be an easy decision… but would it really?

Give yourself as much time as you need. [The decorative photo shows a woman holding a mug, facing the camera, but gazing at something to the side. She is wearing a cozy pink sweater and smiling slightly. She looks content, like she's in no hurry.]

At the end of the day, is there anything you need that you don’t already have? 

There may not be a clear answer, but the exploration will provide insight.

4. What are you holding on to, and why?

When we hold on to anything—a job, a relationship, an identity, a habit—it’s because it gives us something.

What is that thing for you? Maybe it’s the perceived security of a steady paycheck. Maybe it’s the relationships you’ve built. Maybe it’s the idea that it could still work out.

Whatever it is, identify it.

In the end, only you can decide when you’re ready.

I thought the second I had my husband’s support to leave, I’d hit the ground running. But I wasn’t ready. And although it was a really hard year, in the end, I’m glad I gave it the time I needed.

Life is complex, and we try to logic it out with our pro/con lists, but they may not tell us the whole truth.

Friends and family may say it should be an easy choice. Let them.

For that matter, you may be frustrated with yourself, wondering why you can’t see the way forward. Give yourself some grace. When you have been ambivalent for years, it is unrealistic to expect that gravity to go away overnight.

Give yourself the gift of time. 

Keep seeking clarity. Keep preparing to the best of your ability. And when you are ready, trust that you will know.

*This survey was originally reported by CNBC, and was referenced in a recent episode of Pantsuit Politics.

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