When Your Career Is Comfortable, But You Yearn for a Change

You’re at a job that’s comfortable and secure and, frankly, fairly easy in many ways. There might be a few elements that you don’t really like, but for the most part, it’s fine.

Here’s the catch, though: You’re still pretty unhappy at work. You don’t enjoy going to work. You don’t enjoy most of the things you do at work. The little problems at work are like little pebbles in your shoes, building a minor issue into something that’s almost intolerable. Perhaps you simply yearn to be doing something different, maybe something a little more challenging or something that’s a little less stressful.

Does this sound like you?

It certainly sounds like my own situation several years ago. I held down a job that was about 20% interesting tasks, 20% meetings, 15% tangling with bureaucracy, 25% maintenance, and 20% travel. I really enjoyed the 20% of my work that was interesting and I enjoyed my relationship with my coworkers, but I basically dreaded the rest of the job.

I tried a number of different approaches, most of which I’ll talk about below, but eventually I decided that a career change was the right decision for me. I now work from home as a freelance writer, and it was perhaps the best professional decision I’ve ever made, flipping those percentages around to a proportion that I am very happy with (I’d call it about 70% interesting work, 0% meeting, 10% tangling with bureaucracy, 20% maintenance, and 0% travel). (However, that path came with a catch: It involved a big drop in income for quite a while – an issue we’ll get back to in a bit.)

At the same time, I have a few friends – and quite a few readers – who find themselves at a similar crossroads, and simply switching careers isn’t necessarily the best option for them. Every situation is different – some people in this situation are young and some are old, some have a ton of financial responsibilities while others have few, some have skills that are easily transferable, while others do not.

Here are six strategies you might want to consider if you’re in a comfortable place in your career but you’re yearning for a change.

Stick With It

The first and most obvious option is to simply stick with your current job and current career trajectory. While this might not seem like a great choice, if you do it in a smart fashion, it can be quite worthwhile. Your job provides security and good pay and benefits and it’s at least comfortable if not exciting.

There are a few things you can do here to accentuate the positives and minimize the negatives without putting your job at risk, though.

First of all, you can simply start spending a little less and putting more away for retirement. Just bump up your retirement contributions at work and look for a few simple ways in your life to cut back, like buying store brand dish soap. Having a financial target can put a light at the end of the tunnel like nothing else.

Another tactic is to master contentment. Don’t spend your time dwelling on the irritating aspects of your life. Rather, spend your time looking at the good things in your life. One practical way to work on this is to start a gratitude journal. Each day, simply list five things about your life that you’re grateful for, particularly things you noticed within the last day, and intentionally not repeating anything more often than once per week.

A third tactic is use your non-working time with more purpose. Rather than coming home and crashing, find something purposeful to do with that time. Volunteer work? A serious hobby? Community involvement? Figure out a thing or two that you really want to get involved with in your life and start committing time and energy to it rather than just going home and vegetating.

Benefits: You keep your pay and benefits. You keep the security.

Drawbacks: You’re still stuck where you are and generally unhappy with it.

Strategy in a Nutshell: Start spending less than you earn and saving aggressively for retirement, perhaps even an early retirement.

Talk to Your Boss About New Projects

Even the best job in the world can sometimes become boring and routine, and for people who relish challenges, that can lead to a sense of unhappiness. The solution is pretty easy, though: Find a new challenge within the framework of your job.

If you want to largely keep things as they are but would like some new challenges at work, just sit down and talk to your boss about helping you find those new challenges. What kind of projects can you take on? What kind of tweaks to your current work can you handle?

My strong recommendation is to have a realistic and well-considered idea of what you might want to actually do at work that you’re not currently doing. What kind of project do you have in mind? Spend some time envisioning what exactly you’d like to be doing and, perhaps even more importantly, how it would benefit the organization more than it would cost the organization.

For example, in my previous job as a programmer, I would often take on different side projects and fill up as much as half of my week with them. I’d contribute to key open source projects that we relied on. I’d rewrite and optimize some of the underlying software libraries that we used, just to make everything a little bit faster. I’d thoroughly document everything and, near the end of my tenure there, I converted all of that into a wiki. The goal was to find new challenges as much as I reasonably could and it helped greatly.

Trust me: if you are a valued employee who has a record of producing good work, your boss will likely be supportive of your desire to find new challenges at work. Just make sure that you have some clear ideas and an explanation of how they’ll be beneficial to the business without detracting from your other responsibilities.

Benefits: You keep your pay and benefits. Your job is still pretty secure. You’ll take on some new and interesting challenges.

Drawbacks: You might have a little less security than simply doing nothing at all, as there is a risk that you fail at the new projects if you and your boss don’t pick appropriate ones.

Strategy in a Nutshell: Meet with your supervisor and keep a positive tone about your current job, but ask for new projects and challenges.

Switch Jobs in the Same Career Path

It may be that you don’t dislike your career as much as you dislike the circumstances of your particular job. Perhaps you’re frustrated by workplace dynamics, or maybe you find yourself doing uninteresting tasks while being regularly turned away from interesting and cutting edge tasks.

If that sounds like your situation, changing jobs within your career path might be a good move. It does come with some risk – you might find that the new workplace is somehow worse than your current one – but there are a number of ways to mitigate that risk and a number of strong benefits of switching to a new job. Let’s consider both.

First of all, there’s a good chance that you may be able to increase your pay by switching jobs. This is a common tactic for people, particularly early in their career, to bump their pay. They jump from job to job, seeking a higher salary. This strategy can still hold true later in one’s career as well. The key, of course, is to not let an increase in pay inflate your lifestyle. If you see a big increase in pay due to a job switch, keep your spending the same and set up a very healthy 401(k) or Roth IRA contribution to gobble up most of the increase.

Second, the actual process of switching jobs can add a bit of risk to your current job. During the process of interviewing, word can get back to your current employer regarding your job search, which can put you on shaky ground at your current job. A good approach here is to start your job search by talking to people you trust in your own professional network and see what they know of. Often, when you use a good mutual contact as a reference, you can get in with a position without your current employer knowing about it.

Finally, don’t burn bridges during this type of transition. Do everything you can to make the transition as smooth as possible. Give notice of your exit and stick by that notice. Don’t destroy any relationships on your way out the door, even if the relationships aren’t all that strong to begin with. You may end up in a situation where you need to move back to this previous employer or may need a relationship with one of your fellow employees there. Don’t destroy those things in a desire to vent all of your feelings as you exit.

Benefits: You have a good chance at increasing your pay. You get a fresh start within your current career path.

Drawbacks: There is some risk in switching jobs, both in the applying and interview process and whether the new job is a good fit for you.

Strategy in a Nutshell: Quietly check your professional network for opportunities. Apply for new jobs when they truly seem like compelling opportunities. Don’t burn bridges at your current job.

De-Emphasize Your Job’s Place in Your Life

This is a surprisingly effective strategy if you have a job that doesn’t require much of your effort to do well. Many people find themselves in a “maintenance” position that they can handle easily and thus only have to actually “work” a small number of hours per week, or the work that they do doesn’t require intense effort on their part.

If that sounds like you, start considering your work as something you do to support the main focus of your life, rather than letting the work be the focus.

I have a friend who has a job as a loan officer at a bank. His focus, however, is on his church and his community, where he is a leader. He focuses his thoughts and energy on those two communities, even doing tasks related to them while at work if there’s nothing else to do. He views his job purely as a way to obtain the resources he needs to do the things he cares most about.

This can be a great strategy to use if you have something else you want to focus your energy on, whether it’s something that will never return a financial reward (like charitable work or community building) or something that requires a very long runway (like writing science fiction novels or designing board games).

The challenge, of course, is that it can become obvious at work that your focus isn’t on the workplace. If you’re able to maintain your quality of work while doing this, then that’s great; if you’re not, then you can end up putting your job at risk. The real risk is when your work starts slipping and you don’t notice it because your focus is elsewhere. Be attentive to performance reviews if you’re taking this approach.

Benefits: You keep your pay and benefits. You can focus your energy and thoughts on something else that’s more important to you.

Drawbacks: Your job is probably going to become less secure, especially over time, as you move close to doing the minimum at work.

Strategy in a Nutshell: Find another area of your life to focus on. Figure out ways to use downtime at work to accentuate that focus. Stop worrying about work when you’re not there. Spend less than you earn and save the difference so that you have a cushion against the risk of a downturn in your career.

Start a Side Gig

Some people have the entrepreneurship bug and dream of starting their own business where they can set their own hours and decide for themselves what needs to be done. The dream of owning a restaurant or a lawn care business or a comic book store or a Youtube channel runs deep in some people, but they believe they don’t have the opportunity to make it happen.

The truth is you can always make entrepreneurship happen. There are always avenues to use your spare time doing something you enjoy by your own rules and make money. It might take a long time and might not earn a lot of money per hour (especially at first), but it gives you a sense of control and self-determination that you can’t get as an employee, and some people yearn for that.

For those who don’t want the risk of entrepreneurship, another side gig option is to simply take on a second job or some form of consulting related to your career path. Those opportunities are safer, but in many career paths, they won’t earn as much as your main career path.

Naturally, the disadvantage here comes from figuratively burning the candle at both ends. It takes a lot of time and energy to make entrepreneurship work, and the same is true for a second job.

Benefits: You keep your pay and benefits. You gain some interesting challenges and likely some additional pay.

Drawbacks: You run the risk of burnout as you’re essentially adding a second job to the mix. You likely slightly decrease your security at work as your effort devoted to work slips a little.

Strategy in a Nutshell: Find something that meshes your skills with something you’re interested in. Dive into doing that in your spare time. Worry about making money later – start by doing something of value first.

Go Back to School

A final option is to simply reboot your career by going back to school for education in a new career path that’s more in line with what you’ve discovered about yourself since your teen years (where many people made career choices before realizing who they actually were).

For example, one member of my family went back to school in her forties, transitioning from a career in microbiology to a career in nursing. Another friend of mine rebooted his career from teaching into computer programming.

For most, this kind of reboot requires returning to school for some type of education or training. Not only is this often expensive, it also may require a period of no employment, which can be really challenging. Of course, you may be able to obtain much of the education you need during the evenings or weekends to flex around your current career, and community college prices can help lower the costs.

Another concern is that your new career may not be as lucrative as your current one (of course, the opposite may also be true). If this appears to be the case and you’re considering this path, you should cut back on your spending now rather than later and get your finances in healthy shape for this change. Set it as a goal a year or two from now and spend that time planning carefully, minimizing debt, and maximizing savings.

Benefits: You keep your pay and benefits, at least for a while. You’re heading toward a more meaningful and enjoyable career path.

Drawbacks: Your new career might pay less and have fewer benefits, especially at first. The costs of schooling might be intense.

Strategy in a Nutshell: Start spending less than you earn and start saving for the cost of your career change. Figure out what you’d like to study. Seek out evening classes that can get you started on that educational path without causing you to walk away from your current job.

Final Thoughts

If you spend your days dreaming of a big career change in your life, there are many options for making that dream happen. Perhaps you can start from scratch with a fresh education or by starting a side gig. Maybe you can alter your current path by seeking new responsibilities and challenges or finding a new job. Or, perhaps, the best option is to simply stay put.

Whatever it is that you choose, it is far better to have considered the options and settled on the one that works best for you. It’s also worth noting that it’s almost always better to be working for something you care about, even if it’s harder, than to drift through something that just leaves your days feeling empty. The key is to make changes with some financial responsibility and intelligent long-term plans.

Good luck!

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Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.