When to Quit & When to Stick In Your Career - jessdennis.com


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One of the things I’ve done really well in my career is quit. 

Even just saying that feels wrong, like I’m violating some code of business ethics. We all know that to be successful you need to work hard, show up, be consistent and stick it out. 

But do you? What if part of the key to success is knowing when to quit? 

Knowing when to quit doesn’t negate working hard or showing up consistently. Those things can be true and it can also be true that quitting is sometimes necessary. But I think our rejection of quitting is so much deeper than business, I think this is an idea that has been ingrained in all of us from childhood.

I’m a mom…I get it. When I sign my girls up for something new, to give them new experiences, I expect them to give it a fair shake. We’re walking through this right now with dance and horseback riding lessons. My middle daughter wants to be a ballerina. What kind of mom would I be if I didn’t let her at least try? But here’s my expectation: she needs to commit to sticking out of the session. She knows in advance how long the session is so she’s aware of her commitment. If at the end of the session she doesn’t want to do it, she gets to quit! And we all see it as a win! But I don’t think this is the norm. 

We live in a society that values dedication and determination and often, that means we can’t quit. In fact, being called a quitter is an awful thing to be known for, but have you ever stopped to figure out why? What’s wrong with being a quitter? I turned to trusty Google to find the definition of quitter to see if it was negative as we’ve made it or if it was more neutral. Here’s the first definition that popped up: a person who gives up easily or does not have the courage or determination to finish a task.

Yikes! Someone who gives up easily and does not have the COURAGE or DETERMINATION to finish the task! Criminy…no wonder we do everything to avoid this label!

But what if I told you that to thrive, find your purpose, true fulfillment, and meaning in your life, you’re going to have to become a quitter? 

I’m definitely a quitter. I try many things and I quit a lot of them. In fact, I quit all of them eventually. The thing is, most people wouldn’t define what I do as quitting because they’re viewing it from the outside, and perception versus our experiences in it can feel very different! When you’re in it, it still feels like quitting even when you accomplish your goal. Here’s the biggest problem with the previous definition…when do you know if a task is complete? Oftentimes, we don’t determine or define the task at the beginning, so we don’t even know what the task is. 

Many of you have heard my story about my experience in the direct sales industry with my first company. My goal was to make $1M dollars. I did that and like a light switch, I was done. I stuck it out for years because I viewed leaving as quitting or being irresponsible, but I eventually left the company. I quit. Maybe even as you’re hearing me say that you’re thinking to yourself, “you didn’t quit, you just walked away after you achieved the goal”, but let me explain. When you build a company to the point that you’re earning a significant income, walking away from that doesn’t make sense to most people, including those closest to you. In this case, my husband.

The thing is – whatever the “task” is, you need to know when it’s complete. So if you’re going into something new, define the task right away.

For my girls, trying out different sports to see if they like them is the task. If I’m investing in a one-day camp, a four-week session or an entire season, they are expected to stick it out (within reason of course). The task is to play, to try, to experiment. They may feel like this task has been completed at the end of the commitment, or they may want to experiment more and sign up for something again.

The biggest problem with our stigma around quitting is that quitting HAS to be an option on the table if we’re stretching and trying new things!

Think about it…if quitting isn’t even on the table, we won’t try new things. We would only try new things if we knew we’d like them or we knew we’d be good at them. And how will we know that if we don’t allow ourselves to try?


Before we move on, I want to prove to you what a big quitter I am and why I think it’s

been absolutely essential in my journey:

  • 2011: Sold a business I started just three years earlier because my business partner and I weren’t seeing eye to eye, and I couldn’t figure out how to balance raising a baby and a business at the same time. Financially, it worked out. Personally, I lost all of my friends involved in that business and didn’t have a Plan B, so I stayed home with my daughter and obsessed about how everyone likely thought I had given up.
  • 2014: Closed a passion project that I had created with friends – an online micro-donation platform for local nonprofits. Financially, it was a huge failure – tons of investment, zero return. Socially, it helped raise just under $100,000 for local non-profits.
  • 2020: Sold my network marketing business to a friend who then turned around and threatened to sue me. This is a big one. This is the company that I made the $1M dollars with. I was with them for 8.5 years and I just fell out of love with what I was doing. I sold after the Pandemic hit and of course that helped me refocus on our family, but the truth was I had been ready to quit years earlier. The reason I didn’t I want to share with you because I know others are in a similar boat.

Maybe you think the term ‘quitting’ is too strong or not entirely accurate. The other

things we say instead of quitting are transitioning, pivoting, season change, time for a new adventure, retiring, hanging it up. What do you call it? 

We have all these different phrases but they all essentially mean the same thing: we’re stopping one thing to start another. 

The thing is, whatever you call it, it doesn’t make it any easier and often our experience going through it feels like quitting. Even when we’ve accomplished our goals — whatever they are — it can still feel like we’re quitting or giving up early. This is important to talk about because in order to try new things and allow ourselves to experiment, we need to give ourselves permission to quit. If you prefer to call it something else like “transition”, be my guest, but know that it will feel like quitting and some in your network may criticize you for quitting. 

Yes, that actually happens.


Whenever I’ve come to a period in my life where quitting is the right next step there have been similar signs:

  1. The biggest symptom I experience is a feeling. I always feel low on energy and generally uninspired. These feelings can lead to despondency, situational depression, a desire to want to escape and a dreaded feeling of hopelessness or meaninglessness. Those are strong words, but I know you know what I’m talking about, we’ve all been there. How do you know when you’ve gotten to this point? For me, I start dreaming of vacations, I literally dream about escaping. I’ll also find myself abnormally low on motivation – so I won’t want to get out of bed in the morning or take care of myself and my health. These seasons are also typically marked with increased alcohol intake, again escaping.
  2. Another symptom is paranoia. I worry that other people are talking about me and the paranoia leads to a desire to want to be nice to everyone in an effort to be liked. I’ll also start working really hard to please people in hopes that they see how valuable I am or that the work I’m doing is necessary. Essentially, I want them to see that I’m pulling my weight. The important thing here is that they haven’t told me there’s a problem, it’s all made up in my head and it’s total paranoia and it makes me crazy. It’s an awful feeling to worry that other people are talking about you or don’t like you, it’s awful.
  3. Along the same lines of paranoia, I’ll also start doing a lot of comparisons and harboring resentment. I’ll compare where I’m at in life with others (typically online) and I’ll resent people who are further in the direction I want to be. This is ugly and hard to admit but it has a silver lining. When we feel that from others, because we will, it helps to recognize that they may be hurting and whatever we’re experiencing from them is a result of that hurt.
  4. If things go too far I’ll also experience physical symptoms like stomach pain, IBS (sorry, had to go there), ulcers, sleeplessness, heartburn, acne, and fatigue. Our bodies literally start shutting down from stress and they send us signs that things need to change.

So what happens when you feel this way? Obviously with the list above you’d think

someone would just quit but the reality is none of the above symptoms just happen overnight. You’ve probably experienced some or all of these things when something in your life has had to come to an end.

You literally feel sick about it. But it happens so gradually that you just learn to live with it, right? I’d be willing to bet that a lot of us are living in silent misery with all of the emotional, mental, and physical symptoms, but we have started to think of it as our “new normal”. It’s not easy to fight those feelings, especially when you have people in your life who are feeding into the insecurity — the little part of you that still thinks maybe quitting isn’t the right thing to do.

It takes an incredible amount of courage to speak up for yourself and recognize when a season has passed or when something is no longer serving you. If you’re struggling with the HOW (How am I going to get paid? How am I going to sell this business? How do I even start?), find someone in your life who has walked a similar path and ask them to help you objectively think through all of the things that are swimming around in your brain. If you are going to allow yourself to experiment in life and try new things and try to find the thing that lights you up and gives you purpose, know what the task is, but always give yourself permission to quit. Just because you’re starting something new, doesn’t mean you have to do it forever. 

If this has resonated with you and you feel like you’re on the edge of moving onto the next adventure, ask yourself “is my heart still in it?” If your heart isn’t in it, it’s probably time to walk away.

And if you need an extra kick, join me in reading/listening to The Subtle Art of Not Giving a F*ck by Mark Manson. Think of it as a virtual book club! In the book, instead of asking “What will make me happy?”, Mark says a better question is “What pain am I willing to endure in life?” For me, I am willing to go through a little bit of pain every day in service of reaching my biggest goals. Growth doesn’t happen in comfort. So what pain are you willing to endure in order to have the life you envision for yourself?

Please know that it’s okay to walk away, it’s okay to quit. Your biggest criticism will come from those who haven’t mustered the courage to do it themselves in an area in their life that’s causing them great dissatisfaction. So give them grace, give yourself grace, and keep moving forward on your path.

Blog, Business & Entrepreneurship, Finding Balance, Sales, Self-Care & Skincare




When to Quit & When to Stick In Your Career

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