7 Steps For Quitting Like A Winner

7 Steps For Quitting Like A Winner

I received a lot of responses to my article, My Office Repeatedly Contacted Me During My Wedding Weekend Because Nothing Is Sacred. First, thanks to everyone who read, shared, liked, and commented. I have been wanting to tell that story for a while, and I was truly moved by the universality of the experience.

A question I was often asked after the article is posted is “Why didn’t you quit?!?”

For those of you who struggle with adult literacy or internet era-induced ADD that prevents you from reading beyond headlines…I did quit. I now own my own business.

When I was a kid, the karate studio I attended with my younger brother had a mantra, “A winner never quits and quitter never wins, I choose to be a winner. HI-YUH!” *snap kick* We’d repeat this at the start of every class.

Twenty years later, I am here to tell you that is bullshit. (Sorry, Sensei Brandon).

I’ve quit, lots of times. And I am fucking awesome at it. Practice makes perfect. I’ve had a lot of jobs in my adult life and have moved around a ton. I have never been fired or laid off. Each transition was a masterfully planned and executed quit that led to loads more money and better alignment with my goals. I like to call this “points on the board.” Have all these moves ever hurt me in an interview or getting a job? Hell no! (Though today I do kind of wish I made it past yellow belt…oh well). A big part of my business today is helping my clients with similar career transitions.

I know nothing sucks more than being at a job you hate for hours each week. Your unhappiness can seep into everything. As much as you are itching to pull one of these —

Please, try to tone it down. I know you’re suffering, but with a little patience, you will not only get the satisfaction of tap dancing sideways out of there soon, but also knowing your decision is golden and your next move is absolutely ace.

Some of the below may seem obvious, but I see a TON of young people who blow right through one of more of these and sorely regret it more than that fifth drink at a weekday happy hour.

Here is how you too can quit like a winner:

1. Practice Gratitude Daily

I don’t mean to go Tony Robbins new age-y on your straight away. However, the key through getting though any uncomfortable or less than ideal situation is (at least trying to) keep a positive mindset. Your current job may feel like this, but I can pretty much promise you at least one good thing happens each day — even if it’s tiny.

Each day, I want you to write down at least three things you are grateful for at your workplace. Automatic paycheck every two weeks? Health insurance? 401k matching? Easy commute? Hilarious coworker? Boss surprise everyone with a Happy Hour? It can be anything.

2. TIL (Today I learned…)

If you are familiar with Reddit, you may know all about TIL. Each day, even if we are not in our ideal environment, we still have ample opportunity to learn something new every day. Some of our most challenging times and difficult relationships are the best teachers on our paths.

As you go through this transition, I want you to write down at least one thing you learned from your current employment situation. Again, this can be anything — the meaning of a new acronym? A new shortcut in a software program? A public transit shortcut? Why you can’t make ramen in a coffee pot? It could be something in a casual conversation with a coworker or client too. Are they sharing something about their travel, culture, heritage, or hobbies?

3. Prune and Prepare Your Contacts

This is vital. Too many people do not do this. Begin to catalog, organize, and sort all of your business contacts. If you have stray cards laying around, get their information entered into a database. Scarily daunting task? This is something someone on TaskRabbit or a personal VA could easily help with for a small fee. Your network is everything. It can help you find your next position, source an important service, or become the next clients for your new venture. Treat your contacts like cash. Don’t leave business cards lying around; you wouldn’t regularly put $20 bills through the wash or dry cleaner — put them in the bank. Ask for cards when networking — you’re leaving cash on the table!

4. Network

Speaking of networking, it is a must-do. Shy? Introverted? HATE networking? Don’t “know how?” Not to worry, there are different ways to do this based on your temperament and preferences. You can go to in-person events, angle for one-on-one meetings, or contribute to online communities and newsletters in your field.

One way to quickly feel more at ease in a networking event is to volunteer to help run it. That way, you have other activities to busy yourself should you feel overwhelmed. If you’re running a check in table, you also have an easy tip-off point to start a conversation with anyone walking through the door. Shifting your mindset from attendee to host can do wonders for your confidence at a business event.

On another note, ladies — dress practically. You do not want to be sidelined because your heels ache. I am not suggesting you rock your grandma’s Easy Spirit kicks. Consider a wedge, flats, or my favorite the Nike Air line of Cole Haan heels.

Also, check your bag. You do not want to be awkwardly rummaging in the black hole that is your Longchamp to fish out a card that has gum with a penny and hair attached to it. Chic and streamlined. For my biggest events, I have a Diane Von Furstenberg pencil skirt I wear with two zipper pockets: cards in, cards out. I then ditch schlepping the purse around entirely. Another alternative is a small clutch with a wrist strap.

And for fuck’s sake, NO ONE get too drunk. Yes, people WILL notice and you will be THAT girl, guy, or person. Try cutting your white wine with spritzer (if you can order without embarrassment) and definitely alternate your drinks with water or nurse them.

Whichever activity you choose, pick an amount of time to dedicate to it and DO IT. Aim to attend networking events in your desired industry at least once every other week. (And remember what I said about cards in number 3!)

Nothing can replace face-to-face contact. However, also consider joining at least three LinkedIn Groups focused on your desired industry. Feel free to post clear, specific requests regarding further exploring opportunities in the field with fellow members.

5. Re-read Your Current Employment Contract/Agreement

Woohoo! You have your new dream job in hand and you are O-U-T. Before you drive away in a convertible into the sky a la the end of Grease, make sure you know what you might be leaving on the table (if anything). This is the MOST common mistake I see with the BIGGEST impact.

Did you get a relocation or signing bonus? Reimbursement for continuing education? Stock options? If you leave before a certain time frame you may have to pay all or part of it back. Would you be eligible for a big, fat bonus check or profit distribution just by staying for a few more months? Maybe it’s worth it to stick it out just a tad longer.

Also, look out for non-compete agreements if you are hoping to head to competitor or similar job at a firm you feel is a better fit. And ABSOLUTELY if you are striking out on your own in a similar field. The idea that these are almost always unenforceable is false. And either way, it is not a reason to ignore them. Get a solid understanding of your non-compete if you have one before courting jobs in similar industry. If you accept a competing employer’s offer, go to give your resignation and find out if your non-compete bars you from making the transition— that’s an undesirable situation. An employment attorney will usually take a look at your non-compete for free or a small fee. It can save you much heartache.

6. Get in Touch with What You REALLY Want

It is important to start with the mindset you are going to something not going from something. Think about your desired career in terms of what you do want and don’t limit yourself to past experience or the recommendations of others. You are not your resume of college major. You will be surprised at what is possible, even if you do not have what seems like direct experience.

The CEO of Marriott came from Mercedes-Benz without any hospitality experience. There are countless additional examples. Though these are extremely high-level positions, they demonstrate the idea that you are not bound to an industry. There are ways to transition.

For example, I had been feeling drawn to film for months. I had never worked in the entertainment industry before. Today, I have three independent film clients. I accomplished this in a few months. Your skills, abilities, and talents belong to you. Not your current industry or job. What you bring to the table is more transferrable than you think. Get out a piece of paper and go carte blanche and just write about what you want in your next career, try for five minutes uninterrupted at first. NO telling yourself “no.”

7. Prepare Your Résumé, Cover Letter, and LinkedIn Profile

Simple, but again often overlooked. And yes, today you still need BOTH a resume and LinkedIn profile. I have been pinged for so many job offers based off of my LinkedIn profile. I am sure many people on here have been as well. It is the way modern recruiters operate. See specific tips below:
∙ Update your resume to reflect current experience
∙ Proofread resume for spelling, grammar, and formatting
∙ Do the same for your cover letter
∙ If you do not have LinkedIn, get it. Many more employers will see your LinkedIn profile than your résumé.
∙ Update your LinkedIn profile with your current experience
∙ Fill out the headline
∙ Fill out the summary
∙ Ask for at least three recommendations
∙ No selfies
∙ No fraternity or sorority formals
∙ No casual clothes
∙ No other people in your photo
∙ No photos of you engaged in your hobbies
∙ If you have a shot of yourself speaking at an event or on a panel (aka looking important) consider using it.

Again, I know how bad it can feel to be in job that is awful or has simply run its course. Frustrating, boring, and infuriating all come to mind. Hopefully, the seven steps above give you a place to funnel that energy for positive change.

Happy Quitting, You Winner!

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Caroline Gould is a personal branding expert and career consultant based in Washington, D.C. Her signature program is called Self Discovery School. She also writes a weekly advice column on Post Grad Problems. Submit your question or find out more on

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