How To Know When It’s Time To Leave Your Job

You’ve thought about it – leaving your job for a new career. Maybe the circumstances surrounding your work and career have been changing. Or maybe you’ve acquired a new manager whose ideas conflict with yours. Regardless of the reason, you’re not happy. And you’re sure there’s a better career choice for you. But for some reason, you stay. Sure, you’ve talked to recruiters, and updated your resume, but you haven’t been able to take that final step that puts you in front of a potential new boss. So what’s stopping you? 



You’ve thought about it – leaving your job for a new career. Maybe the circumstances surrounding your work and career have been changing. Or maybe you’ve acquired a new manager whose ideas conflict with yours. Or there’s been a buyout or takeover by a much larger company, who is now imposing their management concepts and protocols, and even worse, you see several layers of duplicate job functions and you know it’s only a matter of time before the layoffs begin.

But for some reason, you stay.

Sure, you’ve talked to recruiters, and updated your resume, but you haven’t been able to take that final step that puts you in front of a potential new boss, to have a serious discussion about making a transition from your current employer to a new one.

So what’s stopping you?

Hey, Welcome back. This is roger Reid with another episode of Successpoint360:

The resistance you feel when confronted with leaving an unrewarding, unsatisfying, or even toxic employer, is usually based on one of two things—and sometimes a combination of both.

First, you’re not completely convinced that your situation won’t eventually return to “normal.” You’re still holding out hope that “things will work out for the best.” Maybe even in your favor. Because that’s what you’re being told. Because it’s HR’s current mantra as they unveil the latest version of the “transition plan.” And they would never misrepresent the reality of your future job security – right?

Second reason? It’s easier to do nothing, to stay right where you are. In many ways—ways that we often take for granted—your current position is a place of refuge. It’s where you go to make your contribution, to receive recognition for what you do. And you take comfort in the presumption of financial security it provides.

And so you wait. To see how bad it gets, telling yourself you’re going to put off the decision until you get a better handle on exactly how things are going to shake out.

If you find yourself in either of these situations, you’re no doubt tired, frustrated, and a little scared. Because you’re letting others make a decision that could change your life. You’ve put the future of your career—your options and opportunity for personal success—into the hands of others. And in spite of what you’re being told, you know many of the decisions to either retain you as an employee or let you go will not be based on your professional merit or past contribution. It could be as simple as a coin toss, or a trade-off between division managers.

And you’re far more valuable than that.

But the pull of the past is strong. You’ve spent years making a place for yourself. You’re comfortable. You enjoy the relationship with your co-workers. Others respect you and value your contribution. And a move means giving all that up. It also means facing the risks of a new boss, a new agenda, a new company bureaucracy.

So you wait.

The question is, how long do you wait?

I’ll answer that question telling you about a real story about a very real person who waited too long to leave, and in the process, destroyed any chance of using the assets he’d acquired during his fourteen-year employment at a fortune five hundred company.

If you haven’t already realized it, I’m talking about myself. And what I have to tell you is not so much about me, as what happened to me in the final stages of leaving the company I’d relied on for my livelihood and my sense of professional identity and direction for all those years. 

Maybe you’ll see some similarities in your own situation, and be able to avoid making the same mistakes I did when transitioning from an employee to a business owner.

Hired right out of college at twenty-two, I went to work for a company called Cutler-Hammer. Unless you’re involved in the electrical control and power distribution industry, the name probably means nothing to you. 

I have to admit, at the time, it didn’t mean a whole lot to me, either. 

But unlike most of the electrical manufacturing companies doing on-campus interviewing of engineering graduates, their pitch was different.

They were looking for sales engineers.

They offered a competitive salary, an annual bonus, a company car, an expense account, and flexible working hours — which meant I didn’t have to show up at the office at eight, and I didn’t have to stay until five.

I would be evaluated on performance, not by how much time I spent sitting at a desk.

Compared to the offers I received from industry giants like Motorola, Texas Instruments, and Allied Chemical, it sounded like a dream job. 

After “negotiating” a start date and a preferred location for my eventual sales assignment, I accepted their offer.

Fast forward ten years later. . .

I was comfortable. 

I had a good relationship with my co-workers, and my consistent history of exceeding quotas, increasing market share, and keeping customers happy had earned me the privilege of “flexible” supervision. 

My manager was a thousand miles away, and as long as I continued to produce great numbers, he left me alone.

But there was a downside.

I was bored.

The challenge was gone from the job, and as I looked into the future, I saw another two decades of redundancy and mental stagnation. 

I began to dream of owning my own business. Tired of being a corporate puppet, I wanted to take charge of my professional destiny, answering to no one but myself.

But in spite of that dream, I held on to my job. Maybe it was the fear of giving up the erroneous security of a regular paycheck. But regardless of the reason, I stayed.

And then I received the letter.

The company had been bought by Eaton Corporation — not just a giant company, but a massive, multi-division, international conglomerate.

The result?

For the next four years, the company I had always known as a secure, enjoyable, and even somewhat predictable workplace was ravaged by nothing less than civil war. 

And in the end, I found myself on the losing side.

Unfortunately, the end did not come quickly.

Rather than recognize the takeover as the perfect time to use the strong relationships I had established to kick-start a non-competitive business within the same industry, I fought back.

The process I was fighting against is called divisionalization. It’s also often called restructuring or reorganizing. Regardless of how it’s described, it can ravage the very fabric of the company’s infrastructure, destroying professional and personal relationships at every level. Which is exactly what it did at Cutler –hammer.

Pitting employee against employee, and manager against manager, each knew that for every surviving position within the company, there were at least two qualified, experienced candidates — one of whom had to be eliminated.

I remember hearing managers joke about how the attrition was being handled, suggesting many of us were walking around with a huge red “X” on our foreheads.

“He’s a marked man,” they would say, or “Hey, I’ll trade you three division heads for a regional supervisor.”

But trivializing the situation could not white-wash the professional slaughter.

Instead of handling personnel changes and terminations with dignity and professional respect, some employees were subjected to hostile innuendo and outright confrontation. 

One technique was to question, and even dispute, an employee’s professional ability — an overt and intentional act meant to discredit them in front of customers and co-workers.

For three years, I battled the politics, the personal power struggles, and the clandestine back-stabbing, believing I was doing the right thing. 

Stanchly defending myself and my co-workers, I was quick to point out the hidden agendas and covert motivations of those determined to retain their position by eliminating the competition — by any means necessary.

I felt my actions were justified, not only from my own subjective reasoning, but because I was receiving the moral support of my boss, as well as other mid and upper management personnel, who also felt the divisionalization of the company was wrong.

But over time, my allies became targets in the takeover, and when my boss and his professional equals and superiors— the ones who had protected and shielded me from the carnage — either left the company or were reassigned to other divisions, I became vulnerable.

Without a single remaining friend in high places, there was no one left with enough authority to save me.

So when the time was right — when the corporate lawyers were sure company liability was at its lowest — the opposition struck, unleashing an organized effort to push me out.

The initial attack came during a lunch meeting attended by managers and employees from both divisions, who were now openly warring with each other over customers, product lines, and market territories. 

During the meal, a particularly arrogant manager for the opposition did not suggest or infer, but rather flatly stated I was nothing more than a straw-boss, and would soon be replaced by one of his people.

I didn’t take his accusations sitting down.

I demanded he substantiate his claim and reveal who had instructed him to make such a statement.

He simply smiled and continued chatting about how he found the new structure very promising for those who “understood” the transitioning regime and its long-term goals.

Ultimately, he was right.

About a year later, I resigned, realizing I had nothing left to fight for — my future was somewhere else.

That last year was infuriating, exasperating, and disorienting. 

Every new attack on my character prompted me to counter-attack, to challenge anyone — regardless of their status within the company — to back up their accusations and bogus criticism.

And I did it not only when the assaults were aimed at me, but also when the cross-hairs fell on my co-working friends.

They were just as confused as I was, but not as vocal. And I was often asked to find out as much as I could about how the takeover would ultimately affect their jobs.

Here’s what I want to pass along from that experience.

As an employee, the probability of your future employment is at the whim and discretion of all levels of management above you. 

Trying to satisfy the idiosyncrasies of every member of the hierarchy is impossible — especially when each usually has a personal or even secret agenda.

But that doesn’t mean you give up.

Because while your performance is an important criterion in maintaining your employment under normal conditions, no company continues to operate under normal conditions for very long. 

There are ups and downs in productivity, swings in the economy, changes in the competition, and, of course, internal battles for control.

So while you may believe you can increase your job security with outstanding performance, always remember there are many others with equal talent and ability. 

You’ll keep your job by creating value for your supervisor(s), so determine how they recognize and evaluate your contribution.

For all you know, it may have more to do with the cup of coffee you pick up every morning and place on the bosses desk than the meticulously crafted reports you generate, or your continuing pattern of exceeding sales quota.

As an employee, decisions concerning your longevity are ultimately not your own. The process of hiring and firing is fraught with personality clashes, cronyism, and even physical attraction.

Here’s the takeaway, the bottom line:

During my last year with Cutler-Hamer, I didn’t just burn my bridges, I vaporized them.

The day I left, I turned my back on fourteen years of valuable associations. 

If I’d been smart, I would have identified those managers and division heads who could have helped me by providing the value of their influence and recommendation.

Here are a few suggestions for anyone involved in a similar situation:

You should never outright “leave” a company. 

Instead, make a transition. 

Keep your contacts, both within and outside the company, in good or at least salvageable condition. Avoid revealing any hint of animosity or bitterness — even when it’s deserved. Your revenge will come in the form of the success you’ll enjoy from the new position or company you create for yourself.

Consider your manager as a personal asset. 

Your boss is a source of industry information that can easily translate into dollars and cents. Obtain permission to use her as a reference (after you’ve announced your transition). 

Even better, ask for a letter of recommendation on the day you inform your supervisor of your plans. Even if you have no intention of using it, getting your boss committed on paper means she’ll be less likely to change her mind later.

Once you’ve decided to leave, put the priority on your future. 

Continue to do your job, but if you have a new idea that will increase market share, or have designed a product or service that is similar or competitive, save it — and take it with you. 

It will make you more valuable regardless of whether you go to work for the competition or start your own business. 

As a side note, always check the details of any non-compete and non-disclosure agreements to determine what is considered proprietary. If there’s any chance of infringement or possible accusations of appropriating intellectual property, have an attorney review your situation.

As soon as you make the decision to leave, try to buy as much time as possible. 

You want to make sure your actual termination date is one of your choosing, and not one that catches you by surprise. 

Never give any indication of your intention to terminate your relationship unless you are ready to go, which can literally turn out to be the same day.

Although you may feel a professional or personal responsibility to give your employer lots of notice, it isn’t uncommon — especially in large corporations — to dismiss an employee immediately upon receiving a letter of resignation or even verbal confirmation you’re planning to move on. 

And that means leaving the property within the hour. No ceremony, no good-byes, and not even a hint of cake and ice cream.

Have a Contingency Plan

Prepare for your eventual exit by getting to know the competition. 

Attend trade shows within your industry. The more people you know, the more contacts you’ll have to draw from, if and when you need them.

It’s not realistic to assume the positive atmosphere and comfort level you enjoy from your current position will continue indefinitely. 

Changes can occur at any time, and while some may be only minor alterations to the existing policy or procedures, others can bring about a complete overhaul of the company, eliminating your job and your future with that employer.

Remember, at the start of this episode, I posed the question: How do you know when it’s time to leave?

When the reality of your job no longer accommodates your expectations. It means leaving on your terms, on your schedule. Waiting until you’re given an ultimatum, or being forced to quit because you’re not wanted in the workplace puts you at a tremendous disadvantage.

Remember, it’s your life first. You don’t owe any more loyalty to your employer than what is being reciprocated. And when the circumstances or situation calls for it, employers will not hesitate to terminate. And listen carefully: Letting you go may have nothing to do with the quality of your work or your productivity. It may simply be the result of consolidating branches, offices, or locations. It could be an austerity measure, due to a change in the economy. Whatever the reason, understand that regardless of how much you think you’re appreciated and valued, your employer will cut you loose without hesitation if it serves their purpose in either the short or the long term.

So when you’re ready, make your plan, choose your time, and on the appointed day, give your notice, and walk out the door.

How do you know you’re making the right decision?

When you can look into the future a month down the road, and you no longer see yourself still connected, still associated with your current place and situation. There is only the image of yourself, a bit uncertain, a little anxious, and missing the trappings of a familiar desk, the company car, the paneled office walls, and the long, oak conference table where you presented dozens of proposals.

But slowly, you begin to realize those things were just tools, fixtures from your past, and no longer a part of who you are.

And it feels right.

And maybe, just maybe, it’s accompanied with a sense of relief.

Hey, that’s it for this episode. As usual, there’s a transcript available at Just click on the link under the appropriate episode.  If you have questions or comments, you’ll find a voice mail button in the main menu header on the successpoint360 website.

Thanks very much for listening, and I ‘ll see you next time.

© 2020, Roger A. Reid