Before Leaving Your Job, Ask Three Questions.

In April, over 4 million people quit their jobs.

That’s four million people who woke up the next day wondering, “What do I do next?”

What’s even more interesting is that April was not an anomaly. It follows a trend of the months before where millions and millions of people simply quit, walking away from their jobs.

At the same time, we’re noticing another trend. Some folks who quit their jobs are discovering the grass isn’t always greener on the other side. Many of them are returning to their former employers.

All of this reinforces how tricky a career change can be. A decision like this involves risk, emotions and, of course, money. It’s why I want to offer three questions to think through if you’re considering a change like this.

Think of these questions as a check-list helping you manage the risk of the decision. We can’t eliminate risk but we can reduce it. Sometimes, the riskiest decision isn’t to leave. Sometimes, the riskiest decision is to stay.

But how do you know? How can you shrink the risk gap and move forward with both confidence and peace? After all, we all want to sleep at night, right? I’m not suggesting fear, risk and uncertainty will go away. Nor am I suggesting that these questions will ensure you made the right decision.

What I am suggesting is that questions like these can help you put yourself in the position to make the best decision possible. You can’t predict the future. Neither can I.

But what we can do is shrink the risk gap of a career change. It doesn’t have to be a leap across the Grand Canyon. It can be more like a leap over a mud puddle. Sure, you might get a little muddy in the process but you’re not plunging thousands of feet below.

One other quick note before sharing these questions. For some of us, we didn’t quit our jobs. Our jobs quit us. First, I know how painful that can be. It’s why I’m so glad you’re reading this. These questions can help you too. Your timeline might look different but these questions can help you just as well.

1. Who can I talk to that can help me? 
There’s a Biblical principle that says, “Plans fail for lack of counsel, but with many advisors they succeed.”  For a number of years now, I have had a personal board of advisors who have advised me on both the big and small decisions in my life. It’s a group of four older men (and if they’re reading this, MUCH older) who I look up to and respect.

When I made the decision to leave Gwinnett Church, a church I helped start back in 2011, my advisors were a part of that journey. In fact, it was an 18-month decision-making process that they were involved with the entire time.

Additionally, there’s another principle here that is helpful to keep in mind. Your net worth is often determined by your network.

The old adage is true –> who you know is often more important than what you know. One of the best strategies you can implement while contemplating or being in a career change is to meet with people and ask for their counsel. “What would you do if you were me?” is a great question to ask folks like this, especially those who are further along in life.

Make a list. Then, make the calls.

2. What is my biggest risk?
Often, our biggest risk is money followed closely by insurance. We’ve got to have insurance, right? In America, it’s the law. But these realities can often become handcuffs.

For example, when I talk to people about this and the topic of money comes up, I’ll ask, “If you were to walk away from your job today, how much of a financial runway do you have?” Two weeks? Three months? Six months? Often, my question is met with a blank stare and eventually with “I don’t know.”

This lack of clarity is a breeding ground for fear. It’s why so many people hang on to certainty while also allowing their soul to be crushed at a job they hate.

Let’s not let this be our story. Our first step is to define our risk reality. For some, money isn’t the biggest issue. They aren’t clear on what their strengths are, or they aren’t sure about how to launch their dream job. All of this is under the banner of reducing and managing the risk of a career change.

It’s why I’ve created a free assessment called the Career Risk Calculator. This brief assessment will give you a red, yellow or green light with specific action items on how to take next steps. Did I mention it’s free? Simply visit my website:

3. Am I moving toward something or away from something? 
I have a hunch that the reason people return to a job they left is they were running from something versus moving toward a new, compelling vision. When they discover there are problems in the new job too, they often return to the familiar, even if it was dysfunctional.

The way to distinguish between the two is thinking about which emotion you’re experiencing more: frustration or excitement?

Are you more frustrated over your current situation?
Or, are you more excited about the potential of what’s next?

This takes some honest, self-reflection but whatever you find, the best next step is to keep moving. How can you reduce the frustration and ramp up the excitement?

That’s one of the reasons I’ve written my upcoming book, What to do Next. It’s a practical guide helping you determine your best next step so that you can move toward something rather than running from something.

The book releases in August and can be pre-ordered here:

Click Here to Pre-order
Whether you’re among the four million people in April who made a career change or not, the truth for all of us is that what’s next is on the way. Life is a collection of seasons and you’re in one right now.

One of the best gifts you can give yourself is to start preparing for that next season. Questions like these can help you prepare. As the old adage says, “When the student is ready, the teacher will appear.”

Take a step toward that by answering these three questions today. It might just be one pivotal step toward what’s next.

FOR You,
Jeff Henderson

Leave a Comment