Thinking of Leaving a Secure Job? Here are Five Questions to Consider

I have a number of friends who are considering leaving their jobs this year. That’s not surprising, because a lot of people have left their jobs this year. The reasons are varied, but a lot of it comes down to burnout. Many of my friends work in public education and are worn out over the many challenges that come with teaching: state testing, a constant churn of new district initiatives, inadequate time to plan, endless meetings, micromanagement, parent issues, student issues, inadequate pay … you get the idea. I have other friends in both the public and private sector who are also considering quitting, often because they are overworked and understaffed.

But many of them also have steady, secure jobs. Teaching, for example, is in high demand, and between that and the fact that many of my friends have tenure, most are not at risk of getting laid off anytime soon. Some of my teaching friends also live in suburban areas where the pay is better. The same goes for nurses, first responders, and essential government services.

In fact, that’s often part of the problem: secure jobs are frequently secure because they’re hard. Nothing creates job security like a job that is hard to staff. People who armchair quarterback about these jobs (i.e. “teachers get the summers off!” “firefighters don’t even fight fires most of the time!”) themselves don’t have those jobs for a reason.

If you have a secure job but are burned out, I’m sure you’ve thought of all the reasons why you should stay. Maybe your reasons relate to “golden handcuffs” such as good pay, good benefits, or possibly a pension system or generous employee match. Maybe you like some parts of your job. Maybe you like your co-workers.

Regardless, you’re probably here because there are a lot of reasons why you don’t want to stay. But maybe you’re conflicted. On one hand, you would really like it if someone would just tell you “go, chase your dreams!” but you also know it would be good for someone to be a real voice to say “here’s what you need to consider first.” I’m not you, and I don’t know your exact situation (no one outside of yourself and your closest advisors do), but I can spell out a few key questions to think about as you navigate these waters.

Question 1: What is your dream job scenario?

The most important thing to do before making any job change is to figure out what you want. Do you like your current work and just wish your situation wasn’t as toxic? Or do you wish you were in a different role or profession entirely? (If you wish you could win the lottery and not work, I can’t help you with that, and to be honest you probably wouldn’t be happy anyway.)

These are important questions because it’s not enough just to run from a job — you need to have a destination, too. And you want a destination that is both better than your current situation and, ideally, one that can pay the bills.

I recommend taking some time to sketch out some thoughts on paper. Not on a laptop, tablet, or phone: on paper. Create a list if you want, or a chart or diagram. List out the elements of a dream job for you. The kind of work you’d be doing. Think about what is meaningful for you, the kinds of things that get you in a tunnel where the rest of the world stops. For me, it’s writing. For one of my relatives, it’s visiting with elderly people. For a friend, it’s artwork. For another friend, it’s analyzing spreadsheets and solving financial problems. Maybe your work is in your field, or maybe it is in another field entirely.

You can also think about other parts of the job. How much pay would be enough. How much work-life balance you have. Where you would work. Opportunities for advancement. And, of course, how secure the job would be compared to your current job. Sketch out as much as you can about the ideal job situation.

Once you’ve established your dream job scenario, step back and ask yourself: is this realistic? Does this job exist, and do real people have it? Some jobs, unfortunately, just have problems that come with them. You might be able to make those problems easier, but you may not easily be able to eradicate them. That doesn’t mean you can’t look to move into a job close to your ideals: it does mean you may have to make some trade-offs along the way.

One trade-off might be job security, the very thing that may be keeping you where you’re at. I’ll revisit that later on.

Question 2: What do you need to do to safely get to your dream job scenario?

In an ideal world, your dream job scenario is just a step away. In reality, though, most dream scenarios require extra work, especially if you want to do it in a way that keeps the lights on. Not everyone has the time or money or energy to do that work, and that’s okay. Everyone’s different. But if you have the resources to get to your scenario, many things are possible.

For most people, the key bridge to a better situation is getting the right qualifications, the right skills, and / or the right situation.

  • By qualifications, I’m talking about credentials or work experience. If your job requires a certification — police officer, teacher, nurse, realtor — you’ll need to seek out that certification, which may involve additional education or could just involve a test. If your job requires more schooling, you’ll need to take the required classes. If your job requires a test, you’ll want to look into the test and what it takes to pass. If it requires prior experience, you’ll need to figure out how to get that experience.
  • By skills, I’m talking about the ability to do the job well enough to gain meaningful employment. This is especially true in creative professions. I know many friends who are aspiring artists, but getting to a level of skill that can actually generate significant income takes years of practice and hard work. As Stephen King famously said, there are no shortcuts.
  • By situation, I’m talking about having the right circumstances to get the job. If you want to be self-employed, it’s about growing a side hustle to a point where it can become your main hustle. If it’s about getting into a specific industry, it’s about networking with people who can help connect you to the work you want to do.

These three things aren’t just important because they’re necessary to getting the work. They’re also important because they can help you test drive the work. If you think you want to become a nurse but you find you hate parts of the job while going back to school to get a nursing degree, it’s better to learn that before you make a job switch. If you try building a side hustle job for a year or two but it goes nowhere, that may be a sign that your current plan isn’t quite ready yet.

Question 3: Are there alternative options that might make your life better while still being safe?

I think of these as intermediate options. These are options somewhere between “stay at secure job I hate” versus “pursue uncertain dream that I think I’ll love.”

Those intermediate options could include:

  • Pursuing a different position with your current employer. I know a nurse who was burned out but who landed a remote work-from-home job processing insurance information. A teacher who became a literacy coach. The advantage to these moves is that they often keep the same or similar degree of job security while giving you a change of scenery.
  • Pursuing a similar or related position with a different employer. Sometimes a change of scenery can be helpful. I went to college with a friend who became a Catholic priest. After considerable time working in various parishes, he decided he was ready for a change. So he took on work as a military chaplain. It was a little different than what he’d done before, but it was also a good use of his existing skills. All of us know people who took their current skillset to a different place.
  • Building side work while staying in your job. This is a common route for bloggers and other self-employed types. But it can also work in other professions. One of my relatives started out working as a heating and air conditioning repair guy for a company, but he picked up jobs on the side, too. He eventually founded his own HVAC business and today is far more successful than he would have been had he kept working for that company.

Question 4: Is a job change reversible?

When Jeff Bezos and his then-wife MacKenzie drove across the country to found Amazon in 1993, Jeff left a steady hedge fund job to create an experimental website that he believed had a 70% chance of failure. That seems like a big risk … except it wasn’t. Bezos knew that if he failed, he would be able to go back to his old job. He obviously didn’t need to, but the fact that he could go back reduced the risk considerably.

Bezos has used that mantra to guide Amazon’s decision-making process, discussing the difference between two-way doors and one-way doors. Two-way doors are decisions that can be reversed, while one-way doors are decisions that are difficult, if not impossible, to reverse.

A key question to ask yourself is to what extent is your job change reversible. If you left your job, could you come back, either with your current employer or another one? If you came back, would it be in the same role, or a different one? If you left and came back, what would you lose, if anything? The more reversible a situation is, the better situation you’re in to test drive a change of scenery.

It’s helpful to list any potential changes. If it would impact, say, pay or pension, you might want to crunch the numbers to see exactly what that would look like. If it would impact your job functions, you might want to consider what a post-return situation might look like, either with your employer or another one.

Secure jobs are often at least partially reversible because the demand for workers is high. If yours is, that probably gives you more options than someone whose job is a one-way exit.

Question 5: How can you prepare yourself for the anxiety of leaving a secure position?

Leaving a secure position is bound to cause some anxiety. That’s normal, especially if others are dependent on you. But there are things you can do to help with that. They include:

  • Having a clear plan. Draft a timetable and an action plan. This is especially true if you’re going to leave a secure job for self-employment, because you may need to research things like health insurance (Obamacare? Insurance broker?), taxes (Quarterly payments?), and assorted other issues. Having a clear plan, including what to do if problems arise, will help reduce the anxiety.
  • Getting finances in order. If you’re making a major change, you want a healthy savings and as little debt as possible. There are plenty of opinions on how much savings to have, but a good rule of thumb is to have more savings than you need to carry you until you are in a safe financial situation. To do that, you’ll want to take an honest look at your monthly expenses and estimate how long it would take to reach a safe place if things went bad. Many experts say enough savings to cover six months of living expenses is a good start, and a year is better.
  • Reminding yourself how you got there. If you’ve successfully answered Questions 1-4, you’ve already put in considerable legwork to get to where you’re at. Remember that. You’ve created realistic goals, embarked on doing what you needed to do to get the right qualifications and skills, and evaluated how reversible the decision was.

It’s okay to be honest with yourself about the anxieties. Burying them won’t make them go away. Instead, be real. But also be realistic: if you’ve carefully considered your options and planned your change, anxiety is mostly about fear of the unknown at this point.

But hopefully there is excitement, too, about what lies ahead.


Did you make a change from a secure job? How did it go? I’d be interested to hear about it in the comments.

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