When it is Time to Walk Away

If you are reading this — you probably are not the type of person to give up easily. Neither am I. You are ambitious and skilled and continue to push forward regardless of what obstacles are in your way. And that makes you successful. But here’s the secret, sometimes it’s wise to turn your back and walk away. Sure, it’s painful to admit defeat but when you are in a “no win” environment it’s often the only action that can save you and your sanity.

One of the lessons I have learned working in Silicon Valley for the last 15+ years is that it’s ok to walk away. And in many circumstances it’s even healthy.

Sometimes the company or product problems are too great or your manager is too straight-jacket insane to work with. It is often wise to move on and pour your energy into something that has a better chance of being satisfying and creating value for more people.

I have recently done this with Aha! (the new way to create brilliant product strategy and roadmaps) and could not be more thrilled as the business is growing like crazy.

However, there have been a number of times in my own career when I identified a big hairy problem and after struggling against it for at least a year, decided it was best to move on. And every time my life has benefited and I have gone on to create more happiness for myself and others. The key is that I identified the problem, spoke clearly about it with those who could help me resolve it, and only decided to give up when it was obvious that they would not help and I would be better off doing something else.

In those instances, giving up meant looking for a new job and moving on. If you are in a long-term dysfunctional environment, continuing to do the same job and putting up with the same crap is disastrous for you and people who depend on you at work and home.

The problem is that when you try to persevere, you are in survival mode and a personal hell. You just don’t care about the quality of your work and results anymore. Just walk into the local Post Office or DMV to understand what I mean.

Now, I want to acknowledge that for some it’s easier to walk away than for others. Your level of control depends on your career and financial status and I do not want to overlook that. However, I suggest that no matter your situation — you do have the power to pursue a different course which in most cases will ultimately lead to a new job that will improve your life.

Let’s take a look at how you know the time has come to move on. First, let’s start with what creates a happy work environment and job joy. I think that job satisfaction is based on four forms of alignment. The more your job is aligned in each one of these areas — the happier you are.


And here are the signs to look for in each area that may be telling you it’s time to walk away. However, just because you are not aligned does not mean that you can not become so. It’s important to consider how long you have been trying to find alignment and if it’s likely that you will get there.

If you have been struggling for over a year in any one of these areas, it might be time to move in a new direction.

Alignment with ambition
Are you working for a company and in a role that is getting you closer to your goal? This is a fundamental question to ask yourself and unfortunately most people never do. Because without a goal it’s impossible to know if you are headed in the right direction. I often recommend a “goal first” approach to business planning, but it’s also the first place to start as you think about your own direction. If you have never taken the time to write down where you want to be in three, five, and 10 years, now is the time to start.

Alignment with skills
The most enjoyable jobs fully tap our exiting skill sets and challenge us to grown new ones. Are you a master of the domain you are currently working in or are you on your way? If the answer is yes, you are probably fairly satisfied with the work you do. If the answer is no you, your confidence has likely been battered and you are constantly looking over your shoulder. Now, if you are out of your element a good boss and training can counteract any suffering and help you regain your mojo.

Alignment with reward expectations
There are two types of rewards and both are important. Intrinsic rewards are based on the personal fulfillment you get out of a job well done. External rewards include your salary and any other material benefits you receive from your employer. Your reward expectations need to closely match reality for you to be satisfied. If there is a disconnect here for too long, you will grow disenchanted with the work you do or worse. You might not be able to pay your rent or mortgage.

Alignment with boss
It’s in vogue right now to suggest that people do not leave their jobs but instead leave their bosses. As you have already read, there are many reasons for leaving a job that have nothing to do with your boss. However, I agree that an unsupportive boss is at the top of the list driving folks to update their resume. I have left bosses who: chased employees around the office, did not allow their staff to speak with other managers, and threatened retribution when someone quit. Does your boss have your best interests in mind?

If you have misalignment in any one of these areas I suggest you admit it to yourself first. Next, have a conversation with your boss or a trusted adviser in the organization who you think can help you.

I want to be clear that you are responsible for trying to overcome the challenge and owe it to yourself and the organization to try and work through it. But, if you can look at yourself in the mirror and are comfortable saying out loud that you tried, you may need to move to plan B. If there really does not appear to be a way out and your misery is increasing, it’s ok to admit defeat and walk away.

By Brian de Haaff


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