Why I plan to quit in 2021 😬
Digging into the popular advice "winners never quit" and identifying what can actually help each of us win
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Gonna dive into it today—while I’m so happy that you’re spending a part of your holiday week with me, I want to make sure you have plenty of time to jam along to some holiday tunes and enjoy however you’re choosing to this year. 💜
I really thought about doing some holiday-spirited writing for all of you, but the discussion below is very near and dear to my heart and something I wish I had encountered earlier in my life.
Plus, many of you are likely planning to or already setting some goals/intentions for 2021—I believe you’ll find this week’s newsletter very relevant.
So let’s get into this week’s question:
👉 Do winners actually never quit?
I felt compelled to write on this topic a few weeks ago when one of my mentees expressed her fear of quitting to me. She is a designer at Apple and building her own digital business. The time has come for her to quit her full-time job and give the business the love it needs. I asked her why she feared quitting, and she simply responded with, “Because winners never quit!”
These words took me right back to my sophomore year of college. I had been up late every night for toooo many nights contemplating if I should quit a “prestigious” consulting organization. Quitting it was unheard of apparently, and everyone I sought advice from said I’d be foolish to give up the opportunity. Plus, I had worked so hard to get in, in the first place, so why would I want to waste all that effort?
Except it didn’t feel like an opportunity to me. It felt like a huge cost when I compared it to the time I could be spending on the first business I had just started and valued more. And the longer I waited to quit, the larger my opportunity cost became.
When I did finally approach the club’s leadership to resign, I remember he offered a very memorable piece of unsolicited advice, “winners never quit, and quitters never win.”
So, when my mentee mentioned these words, I had to understand why she believed this advice so much. Turns out, she had simply heard them her entire life, especially as an athlete, and prided herself in never quitting. She stuck with almost everything, even if she didn’t enjoy it, just so she could say, “I didn’t give up!”
I asked her, what does quitting mean to you?
She immediately responded, “quitting means giving up!”
Shireen: Giving up what, exactly?
Mentee: Discipline. Opportunity. Just because I don’t like something doesn’t mean I shouldn’t appreciate it and give it up.
Shireen: At this point, do you doubt your ability to practice discipline or gratitude?
Mentee: (thinks) No…
Shireen: Okay, so why else is not quitting important to you?
Mentee: I want to win. I can’t win if I just quit.
Shireen: What does “winning” mean to you?
Mentee: Depends. For my career—knowing I’m doing my best work, feeling challenged, loving what I do and feeling financially free.
Shireen: What will make you feel more of that? Your current job or your business?
She and I both knew her answer before I even finished my sentence. She recognized that she had focused SO much on never quitting that she never gave much thought to what winning should feel like. She had spent years doing things that made her miserable, instead.
I empathize, because I’ve fallen in this trap myself. So I wanted to share how I look at this very popular advice.
Where does this famous advice come from?
From a quick google search, it appears that Vince Lombardi, an American football coach and executive in the National Football League, is credited for this saying.
I didn’t dive too much into the context, because I didn’t feel like I needed to. In the context of a sport, where the literal goal is to win a game, quitting the game won’t give you much of a shot at the win…
I’m also not here to judge Vince Lombardi. I’m not concerned with his statement; I’m concerned with how this advice has been extrapolated.
Similar to my mentee, I also heard this statement all the time growing up. But I’ve now recognized:
“Winners never quit” was helpful advice in many contexts, and harmful in many others. Being thoughtful about your context before applying any piece of advice is critical to your success. (Agree? Share on Twitter)
I can’t tell you how many times I felt like a complete failure every time I chose to quit something. I was deeply programmed to “stick with it” for the sake of practicing follow-through even when I trusted my ability to follow through on commitments. I already had that muscle—it didn’t make sense to keep making myself miserable or giving up more relevant opportunities.
How do I think about “winning”?
It wasn’t until I started my first company and fell in love with my work that I realized I, ironically, had too much to lose if I didn’t quit.
That’s when I committed to questioning the advice every time it popped into my head:
What does winning really look like for me, in this context?
What’s more likely to help me achieve that vision?
I ask these two questions every single time I feel that I’m not using my time wisely or investing my energy in the best direction. I’ve quit projects, relationships, jobs—and I’ve found that I really only regret waiting too long to quit something instead of not sticking with it long enough. I pride myself in “putting in the work,” but only when it’s aligned, even if in some fuzzy way, to my vision of success.
I’ve become very intentional about surrounding myself with people who champion thoughtfulness and iterative decision-making over “sticking with it.” I’ve also become intentional about holding them accountable for it. For example, my mom used to always make fun of the amount of “diets” I’ve experimented with. She’d joke, “one day, you’re drinking soy milk. Then almond. You’re paleo one moment and then pescatarian the other.”
I used to just laugh along.
But then one day, I asked, “It’s because I’m committed to figuring out what works for my body. So if I have to quit diets so I can focus on finding the right fit for me, why shouldn’t I?” My focus was to win at identifying the best nutrition for my body, so I had to be okay with admitting when something wasn’t working and quitting.
So, as I look ahead at 2021, I already know I’ll be quitting quite a few more things. I’ll probably write on each of these down the road, but if you’re curious, I’ve already committed to:
Quit constraining every goal with time limits
Quit looking at the concept of time in the traditional construct
Quit looking at financial currency as the only currency
Quit being afraid to ask questions you think are stupid
Quit thinking in mutually-exclusive terms
I’m curious to hear how each of you feel about “quitting” and if you plan on quitting anything moving forward. As always, you can just reply to this email and share your thoughts.
Thanks for spending a part of your day with me, and happy holidays!
🎁 PARTING GIFTS
A round-up of hand-picked, highly recommended tools, and inspiration to help you live your best life.
"I just try and avoid being stupid. I have a way of handling a lot of problems. I put them on what I call my too-hard pile. Then I just leave them there. I'm not trying to succeed in my too-hard pile."
— Charlie Munger (in this at Caltech last week)
Loved reading about Upstart’s journey from a “fuzzy” idea to IPO. I read this very interesting piece by the CEO, and found Section 5 especially lovely.
"But Larry and Sergey were just so out there in terms of questioning and challenging every assumption you had about how the world is supposed to work," says Girouard. "Everything you learned about how to do a product roadmap, how to specify requirements, how to listen to customers, you could just tear up those playbooks. They had complete confidence in their intuition and their ability to ask questions and do things entirely differently. And that's the magic of why Google is Google."
👋 See you back here next week to explore:
Special Edition: How I’m preparing to be my most thoughtful self yet in 2021
The Human Behind this Newsletter
❓ Got a question you want to unpack together? Tweet me, @shireenjaffer_.
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💜 This newsletter was crafted for you while patiently waiting for some made-from-scratch brownies to finish baking. Share with a friend who makes you feel as wonderful as warm brownies make me feel (hint: VERY!)—and let them know it.