Welcome to the Stop Sabotaging Your Success podcast, episode one hundred and twenty-three. I’m your host, Cindy Esliger. This is the podcast focusing on what we can do today to take control of our careers and overcome the inevitable barriers to success that we encounter along the way. 

Deciding when to do a major career overhaul, that may or may not include quitting your job, is no small feat. It’s akin to standing at a major crossroads, map in hand, with multiple paths winding into the unknown. Each route promises its own set of challenges and rewards, making the choice not just a practical career decision, but a profound personal one as well. 

For many, the decision to stay put or jump ship is fraught with what-ifs and could-be’s, often accompanied by a hefty dose of soul-searching and a lot of after-hours searching for more exciting job postings. Whether it’s the monotonous daily grind that’s wearing you down or the tantalizing possibility of something more lucrative, or at least more fulfilling on the horizon, knowing when to make a move or stay the course can feel overwhelming.

In this episode, we explore this career conundrum because recognizing that you have the ability to choose can be incredibly empowering. While the fear of making the wrong decision tends to paralyze us, the act of deciding for yourself whether to stay or go reclaims your agency in setting the course for your professional life. 

This choice, whether to persevere in your current role or to pursue new opportunities, isn’t just about changing where you work; it’s about aligning your career with your evolving ambitions and values. Understanding when and how to make this pivotal decision involves more than just evaluating your potential job satisfaction. It’s about digging deeper to uncover what truly matters to you and how your work integrates with your larger life goals. 

It’s the question that seems to come up more than any other these days: “Should I quit my job?”. If this query hasn’t popped into your head at least once in the past few years, consider yourself either supremely lucky or blissfully unaware. But, let’s face it, the mere existence of this question suggests a lot is brewing beneath the surface of your daily grind. 

Maybe for you quitting seems like the ultimate liberation, right? Throw your papers in the air, tell your boss what you really think, and walk out, with the door slamming behind you. But, before you do any of that, and burn those bridges beyond repair, keep in mind that your industry is a small world after all, and what might feel amazing in the moment, could come back to haunt you years down the road.

So, before you plan your dramatic exit, let’s unpack the multitude of issues you might be stepping into. Quitting is no small feat, and the reality is, it’s loaded with mental, emotional, and financial baggage that not everyone is ready to handle. 

Your workplace may be like many others, filled with people who are more than just a little frustrated with their jobs. And you may be one of them, not wanting to take it anymore, but knowing you have a multitude of years before you can even consider retirement. Here’s something to consider:  What if you could turn the job you have into the job you love? Groundbreaking, right? Before you scoff, hear me out. 

Imagine you’re stuck in a job that once seemed to check all the boxes, but now feels anything but perfect in your day-to-day life. Or maybe you’re flirting with the idea of going back to school for an advanced degree, or shaking things up in a different way by doing something completely different with the education you’ve already got. That’s a powerful notion, realizing you can actually steer your career ship. But, amidst these secret fantasies about upending your life, it’s worth asking: Is this even possible, or am I just daydreaming? 

Giving your two-weeks’ notice might sound liberating, but its not always practical. We all have bills to pay and career transitions require significant mental, emotional, and financial runway. And, let’s be real, some of us are just too exhausted trying to survive to even ponder how our current skills could be transferable.

But wait–before you think a major life overhaul is off the table, know this: there are simpler paths to improving your job satisfaction. It’s not always about sticking it out or jumping ship. There’s a vast middle ground that you may not have considered. Picture this: keeping your day job while making small-scale changes that actually make you feel better about the work you do and who you do it with. Give that a moment to sink in. 

Maybe you could start with something as simple as a mindset shift. Viewing your work as meaningful can be a game-changer, like realizing that developing design solutions is actually a big deal. Or maybe you could dive into a hobby outside of work to stretch beyond that identity crisis your job has thrust upon you. The kicker? Many of these strategies don’t even require your boss’ nod of approval.

The vital piece here is seeing the possibilities. Just knowing you have options can be incredibly empowering. When you realize job satisfaction is largely in your hands (surprise!) you can start reclaiming the power of your career’s direction. 

Everyone has a career story. Whether you took your job out of necessity or desire, or if what was supposed to be a brief stint turned into a decades long saga, it doesn’t matter. What matters is there’s a path to greater job satisfaction, and it’s not as elusive as it might seem. It starts with discerning what’s within your control and figuring out how to improve it, even incrementally. 

We’ve all overstayed our welcome in jobs that didn’t serve us well. We’ve all had days where we fantasized about burning it all down because nothing went our way. But, if you’re honest, there might still be things about your job that you enjoy, if you’re willing to look hard enough. But, back to the question at hand, “Should I quit my job?”. There is no right answer, only the decision that best aligns with your unique circumstances. 

So, is it time to call it quits? Only you can answer that. It’s about weighing whether quitting is genuinely the best option or if there might be alternative routes worth exploring. Either way, the power is in your hands, not in that resignation letter you spent hours preparing, for just the right moment, that’s burning a hole in your desk drawer. Unless you’ve got a better option waiting in the wings, shouldn’t you at least consider the option of making your current job a tad more bearable before setting your sights on something new? What do you have to lose? If you’re in a toxic work environment, that’s a different story. Get out of there as quickly as you can before it has a lasting impact on your self-confidence. 

Unfortunately, career decisions can be tough, and the path to figuring out if it’s time to walk away involves a lot of uncertainty and fear of the unknown. So, how do you know if it’s time to update your resume or your LinkedIn profile? Let’s break it down into three practical steps: 

Step 1: Assess and Evaluate

First things first, it’s time to play detective in your own career. Start by assessing what’s going well and what’s making you fantasize about dramatically quitting in a blaze of glory. Are you simply jumping on the bandwagon because everyone else is making an exit and you’re afraid of missing out, or do you genuinely crave change? Here’s a couple of things to consider: 

• Benefits of Sticking Around–even if your colleagues are dropping like flies, there could be good reasons to stay. Maybe there’s a promotion on the horizon, or you’re close to completing a major project. And don’t discount the organizational knowledge you’ve acquired in your time there. 
• What Does Success Look Like to You? This isn’t about your parents’ or friends’ definition of success–it’s about what makes you tick. Reflect on whether you see a clear path forward to what you desire or whether you’re getting sidetracked by something that’s shiny and new. 

Use this stage to get clear on your specific career goals and what you actually want out of this job, beyond a paycheck, and whether that’s realistically available to you eventually, should you be willing to put in the time and energy to make it happen.

Step 2: Take Action 

Now that you’ve mapped out what’s bugging you and what you’re aiming for, it’s time to take some action. But let’s focus on implementing some tactical maneuvers before embarking on anything drastic: 

• Craft Your Job–start tweaking your role to include more of what you love and less of what you loathe. If you’re into project management but hate managing project financials, see if you can shift your focus more squarely onto your strengths, while letting someone else worry about the forecasting.
• Tackle the Small Stuff–sometimes it’s the little things that make a job unbearable. Figure out what you can do to lessen those daily annoyances, because there’s always something you can do to make it better. 
• Expand Your Skills–focus on your professional growth by expanding your skillset through formal education, helping out on new projects, or even shadowing a colleague who is doing something you find interesting. 

This stage is all about making your current role as enjoyable as possible while beefing up your resume should you decide to pivot within the organization, or ultimately leave.

Step 3: Give Yourself Options

The final step is all about preparation. Whether you decide to stay or go, you’ll feel much better having a plan in place. 

• Explore Career Development–look for opportunities for advancement within your current organization. Is there a step up that aligns with your career goals? 
• Enjoy Life Beyond Work–consider what else fulfills you outside of work. Maybe you can start a side hustle or dive into a hobby that brings you joy. Expecting your day job to be everything you need is a bit much. 
• Make a Plan–start laying out a plan for making a transition should you decide it’s time to move on. This might include creating a financial runway, updating your resume, networking, and potentially even exploring a different application of your skills in new industries. 

This stage is all about giving yourself options to make you feel empowered and less trapped in your current situation.

In the meantime, now that you’ve uncovered the good and the bad of your current role, you have some choices to make with this newfound awareness: 

• You Can Stay Annoyed–where you continue to focus on everything you hate, but where’s the fun in that? You risk having your productivity plummet, possibly attracting the wrong kind of attention, and forcing your hand before you’re ready. 
• You Can Decide to Leave–where you decide to find a place where your contributions will be more appreciated because you think the challenges of your situation far outweigh the benefits.
• You Can Focus on What Energizes You–where you try to shift your focus towards what you enjoy. Can you delegate or automate the tasks you despise? Can you spend more time on the aspects of the projects that light you up? 

Being aware of what you actually like and dislike about your job is a powerful tool. It can significantly boost your job satisfaction by helping you focus on the positives and manage the negatives more effectively.

But, before you do something rash, consider for a moment that not every irritation requires a job change. Sometimes, a little strategic tweaking is all you need. It’s easy to think that the grass is always greener, but that isn’t always the case. Plus, let’s be honest, even the best jobs aren’t perfect. If you like your job 80% of the time, you might actually have something worth saving. 

Before you pack up your desk, let’s first untangle what you think you should be doing, from what you actually want to be doing. People change and responsibilities evolve over time. Remember, every job will involve some trade-offs. You have to decide what type of misery (or monotony) you’re willing to tolerate and what’s a definite deal-breaker. 

Maybe what you’re feeling is fear–fear of being seen as a quitter, fear of having made a mistake, fear of admitting that maybe this isn’t the right path for you after all. But here’s the thing–quitting your job doesn’t make you a quitter. It makes you someone who is willing to take control of your career and steer it in a direction that brings you more joy and fulfillment. 

Be brutally honest with yourself about why you want to leave. Is it the job, the people, the industry, or just a nagging feeling that you could be doing something more fulfilling. Recognize that creating new opportunities often takes a lot of extra work. If you’re only half-hearted about the change, it’s likely not going to end in the way you’d hoped.

Many stay in unsatisfying jobs because they feel they’ve invested too much time and energy to leave at this point. This is the sunk-cost fallacy. Just because you’ve spent five years in a role doesn’t mean you need to stay five more years to prove anything to anyone. 

Guilt is another sticky issue. Maybe you feel guilty for wanting to leave a job that looks great on paper, pays well, or is seen by others as a ‘dream job’. But, if it’s not your dream, that’s okay. Your career isn’t just a resume; it’s where you spend the majority of your waking hours for many years, which is a significant part of your life. 

One often overlooked aspect when deciding whether to quit a job and possibly pursue a major career overhaul is the concept of ‘opportunity cost’–referring to what you are potentially giving up by staying in your current job. This could include foregoing the chance to develop new skills, engage in more fulfilling work, or even improve your mental and emotional well-being. It’s not just about what you stand to gain by making a change, but what you continue to lose by maintaining the status quo. 

Understanding this can significantly shift the decision-making process, providing a broader perspective on the true impact of staying versus leaving. While many focus on the immediate risks and fears associated with leaving a secure position, they frequently underestimate the cost of staying in a role that no longer advances their professional goals or provides any personal satisfaction.

In the end, whether you decide to stay put, revamp your current role, or pursue new opportunities, the key is to make that decision from a place of strength, not desperation. Make sure it’s a decision that leaves you feeling empowered, not second-guessing yourself. Know yourself, know your worth, and don’t be afraid to make the move that’s right for you. 

After all, it’s your career path–make sure it’s leading where you actually want to go.

And that’s it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Considering a Bold Step at cindyesliger.com/podcast, episode one hundred and twenty-three.

Thank you to our producer, Alex Hochhausen and everyone at Astronomic Audio. Get in touch, I’m on Instagram @cindyesliger and my email address is info@cindyesliger.com.

If you enjoy listening to this podcast, you have to come check out The Confidence Collective. It’s my monthly coaching program where we dig a little deeper into what’s holding you back in your career, and we find the workarounds. We help you overcome the barriers and create the career you want. Join me over at cindyesliger.com/join. I’d love to have you join me in The Confidence Collective. 

Until next week, I’m Cindy Esliger. Thanks for listening.