When Is The Right Time To Quit?

An interesting side effect of deciding to close a business after 15 years is how many people congratulated me on being able to quit. At first, I was surprised by this but then I thought about it and realized how hard we are about the concept of quitting. It also seems to be an incredibly hard action for those who are drawn to entrepreneurship. But it certainly is not a healthy action and should probably be practiced more often.

I’ll be the first to admit that the obsession our culture has on grit and perseverance creates a slightly blinded drive that above all else you must keep going. In theory, perseverance is the answer to success. No matter what, you shouldn’t stop. If you push through the hard part, you’ll win. All you have to do is keep going. This is the thinking that kept me trapped in a business I hated for 5 years too long. It was a carrot that I dangled in front of myself, the idea that as long as I did not quit, everything would work out.

I’m not sure what I even thought “everything would work out” meant. I had lost sight of my goals long before I reached the point of obsessively pushing on. It was the fear of failure and what that would mean to my type A brain that kept me on the hamster wheel. Fortunately, I finally realized that I was forcing myself to keep going and growing in something that I didn’t want to do. Or rather, I was falling apart mentally and physically and I no longer could do what I was doing. My subconscious had to step in do the deciding for me. So I quit.

It’s been over a year since I made the decision to walk away. I have not regretted it for one minute. Not even a thought bubble that I squashed down. Yes, I should have quit sooner, but the timing worked out so no regrets. I’m not at all suggesting that I learned all of the lessons from this decision. I did however learn that it’s not only ok, but that it needs to be part of my routine that I check in regularly and make sure that I’m sticking with things for the right reasons.

Last week, for example, I quit my podcast after only 6 months when I had told myself and my co-host that I would give it a year. I had been reviewing how it was fitting in with my goals, vision, and mission and it was just not there. It was not going how we thought it would go and our numbers reflected this in a glaringly obvious way. Sure, I could have pushed on for the next 6 months, what harm could it have done? But the truth was that every week, I had a gnawing feeling in my gut that it was not working and that I should not be wasting time on something I knew was dead in the water. And more than my gut, people who know what I’m about had started to speak up that it didn’t seem like me. That everything that I’m about what absent from it and they didn’t like it for that reason.

That really struck a cord. So I made the decision to walk away and yes, to quit. Even writing the word makes me shudder a bit and put a weird sort of guilt on myself for it. How’s that for a type A, overachieving (I actually prefer the term go-getter) pressure that is entirely made up in my head? Who else is with me on that??? But seriously, the shift in my mental state and my physicalness was obvious when I ended it. I didn’t realize how much of a negative impact there was of staying with it for the only reason of not quitting.

The brings me to the big question: How do you know when it’s time to really quit instead of pushing through a hard phase to achieve success with something?

  1. You are experiencing more negative than positive with something. If you are constantly frustrated and feeling this way more than you’re feeling rewarded, that’s a big sign. Do you sigh in relief when you think about quitting? You should feel excited optimism about what you are doing more often than excited about quitting. Be aware of the differences between challenges and the opportunity to learn from adversity and no longer caring about the outcome. You need to still be excited about the potential outcome.
  2. Spending time on or in the thing is stopping you from doing more rewarding endeavors or is damaging you. Do you keep saying no to opportunities that you would rather do? This does not mean in a distracting ADD way. This would be more of a turning away your dream job because you feel like you would be failing if you closed your side hustle that has never taken off like you thought it would. Are you drinking or using drugs to deal with the stress of it? Have you stopped sleeping or are relationships suffering from it? If you are having any physical or mental issues due to something, you need to stop it. Toxic relationships included.
  3. Your friends and family keep telling you to quit. They can usually see the forest through trees much better than you can. I have found that I should listen as soon as more than one person close to me tells me that it’s enough.
  4. Your priorities change or you are doing it for the wrong reasons. Sometimes you think you’ll be more into something than you actually are. Think every kid that ends up in law/medical/whatever school because they thought they wanted to be something (or they are doing what their parents wanted) and then get there are not feeling it. The ones that kept pushing are usually pretty miserable with the outcome.
  5. You’re not quitting because of all of the time, money and effort you’ve put in. That’s a valid thought process, but not enough of a reason if any of the above are happening.

Let’s say you realize that it’s time to quit something. Now what?

  1. Take a bit of time to process your decision and try and remove the emotion. We Have all fantasized about throwing work at the boss and storming out. Not the best way to quit a job in the days of social media, LinkedIn and viral word of mouth (or ever). You may also want a recommendation from said boss. Don’t let anger or the elation of leaving fuel your actions. Take some time to check your emotions before you begin your exit.
  2. Take your ego out of it. Do not dwell on feeling like a failure. Instead, focus on what you have learned and how you can use the experience in your next endeavor. Remember that failure is essential to growth. If you never fail, you’re not going big enough.
  3. Have an exit strategy. Especially for those who like a plan. Create a timeline. Work backward from a final date and include everything from telling those directly involved down to what you’ll say on facebook. You can include what your plan of action for moving forward are as well. This could end up being a big huge plan. Don’t be afraid to include as many details as makes you feel like you are ok going forward but also know that you may have to roll with it and cannot control everything that happens during transitions.
  4. Acknowledge the stress of the exit. As someone who has left jobs, been through a divorce and closed a company, be prepared for the emotions, the stress of not knowing what is next for a while and the transitioning. Be easy on yourself. Also, know that if you do not feel all the emotions you or others thought you would, you are not a bad person or dead inside. It will be a weird time. When I closed the business, I kept waiting for the mourning process everyone told me I would experience. It never came. I decided it was due to being less of a death and more of a breakup in an “it’s not you, it’s me” situation.
  5. Accept that quitting may be incredibly difficult and painful. You’ll have people in your life who don’t understand your decision. You may miss the job, project, or person and all of the familiarity of them. It may help to write down why you are quitting to remind yourself when you’re having low moments. And remember that exercise, eating well, self-care and a strong support system can get you through anything!

Knowing When To Quit – NY Times
Why You Sometimes Have To Quit To Win – BBC
How To Know When It’s Time To Quit – Life Hacker
Quit Already – High-Performance Lifestyle
8 Ways You Can Tell It’s Time to Quit – Psychology Today
When to Stick with Something and When to Quit – HBR
How To Know When It’s Time To Quit A Project – Due

1 thought on “When Is The Right Time To Quit?”

  1. Wow! What a powerful piece! I have struggled with this too – knowing when to quit – and sometimes I’ve stayed too long. I really like your personal examples and specific recommendations. Thank you!! P.S. I am going to miss Polarity Podcast…

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