“Should I Stay or Should I Go?”

“Should I Stay or Should I Go?”

“There is a difference between giving up and knowing when you’ve had enough.”


Ever felt the urge to just up and quit?  Quit a job, end a project, stop pursuing a new business or solopreneur venture, when you felt like you’d hit a wall, or when external expectations or pressures became too much?

Did you stay or did you go?

Let’s be clear.  There’s no black and white, right or wrong answer here.  Everyone’s feelings and circumstances are unique.

If you stayed, you may have felt you’d invested too much time and energy into it to stop and move on.  Or, you worried about the financial impact of making a change. 

Maybe you were so passionate about the work, you knew you needed to tough out the bumps in the road.  Or, perhaps you felt some type of external pressure to maintain the status quo.

Whatever the reason, you kept plugging away, trying to make the best of it.  And it either worked itself out or it didn’t.

If it didn’t, the urge to quit may have built up till you felt like you’d burst from the frustration of it all.  You may even feel that way now.

Before you go too crazy from it, consider this: It is natural and normal to grow out of a job or business venture.

It’s like shoes when you’re a kid.  You naturally grow out of them and need to move on to the next size.  If that doesn’t happen in a timely manner, a very uncomfortable feeling takes over, which can eventually become downright painful.

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Ellen Goodman once wrote “There’s a trick to the Graceful Exit. It begins with the vision to recognize when a job, a life stage, a relationship is over – and to let go. It means leaving what’s over without denying its value.”

Those who are willing to quit for the right reasons get to move on to the next phase of their lives or careers.

Right and wrong are in the eye of the beholder, but here are some guidelines to consider.

What are some “right” reasons to consider a move? 

In a 2013 Forbes article, writer Jacquelyn Smith shared 14 Signs It’s Time to Leave Your JobThree years later, these remain classic signs that it’s time to either find ways to improve the situation, come up with an exit strategy, or sometimes both at once. 

While her article is focused on individuals employed by others, many of these signs apply to solopreneurs and small business owners as well. 

A few examples from her list:

Your skills are not being tapped • You lack passion • You’re miserable every [workday] morning • You don’t fit in with the corporate culture and/or you don’t believe in the company anymore • You’re bored and stagnating in your job [or solo venture] • Your ideas are not being heard • Your work-related stress is affecting your physical health.

To these I would add:

Opportunities to learn and grow have dried up • You look at your boss’s job or those a few steps ahead in your industry and you know you don’t want to go there • Your true gifts and talents are wasting away • Your authentic calling is calling out to you.

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It’s up to each individual to decide what the right reasons may be to make a change.  But if either of these is your motivation, it may be best to think twice:

Being in the “messy middle.”

The messy middle is that discomfort zone between starting something new and either attaining a certain level of expertise or achieving a big goal.  Let’s face it – we don’t like the feeling of not knowing what we’re doing.  But if we don’t reach the messy middle from time to time, we’re just not stretching ourselves enough. 

“One of the best things you can do in the messy middle,” says writer and coach Celeste St. Hill, “is to go back to your ‘why.’ What was the original reason you started this? If the why is powerful enough, it will help you move forward again.”  

Fear of failure (or even success)

Being asked to take on more responsibilities and perform at the next level can be a great compliment and confidence boost, but it can also create fear.  As can stepping out into the great unknown as our own boss in a new venture.

Fear of not being up to it, fear of failing, even fear of being found out as an “imposter.” (See Valerie Young’s definitive book The Secret Thoughts of Successful Women, Why Capable People Suffer from the Imposter Syndrome and How to Thrive in Spite of it for more.)

And as Stephen Pressfield writes in The War of Art, even the fear of success that may take us out of our familiar life is not unusual.

Only through honesty with ourselves about our fears can we decide if it’s really time to go and grow, or time to stay and grow.

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If and when you do decide to make a change, make it the “Graceful Exit” Ellen Goodman recommends.  Avoid bridge-burning; it’s a very small world. 

Try to have your next work lined up before ending.  If you’re going solo, start that on the side first and ensure you have the cash flow from it you need to pay the bills. 

If for any extreme reason, you just can’t wait till you have something else, be sure your financials are in order, including having plenty of savings to tide you over.  Don’t put yourself in jeopardy or unnecessarily make things harder for yourself financially.

Acknowledge and be grateful for all the good the situation you’re leaving brought you.  The learning, new experiences, friendships.  Even if the one benefit you can think of at the moment is that it helped you realize what doesn’t work for you.  That can be a huge gift. 

Think of the famous Thomas Edison quote, the ultimate in looking on the bright side and being grateful for the good in what could be seen as a negative situation: “I have not failed. I have just found 10,000 things that do not work!”

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One last thing. 

This kind of decision needs more than dry logic or a list of pros and cons.  We also need to listen to what inspires us, motivates us, and calls us to a sort of joyous action. 

If you’re on the verge of making a change and need a little inspiration, have a look at this Steve Harvey video.  Speaking with his studio audience after taping a show, he made an impassioned case for what he calls “jumping.”

Watch, and see where your thoughts take you.  As Harvey shares:

“You’ve got to identify your gift and jump. Your gift will make room for you. Every successful person in this world has jumped. Eventually you are going to have to jump. You cannot just exist in this life. You have got to try to live. If you’re waking up thinking there’s got to be more to your life, believe it, there is. But to get to that life, you gotta jump. The only way for you to soar is you got to jump.”


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Peggy Fall has been helping match talented people and great companies for years, and is a strong believer in blazing your own trail, creating meaningful work, and living life on your own terms. “There’s a whole range of possibilities out there if we leave old paradigms of ‘how life is’ behind.”

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