When to Quit and When to Double Down

Do I quit, keep going, or double down?

Feb 23, 2018 · 8 min read

Originally published by Stephen Guise on his personal website.

The first time I made this decision in my career was when I quit on the first day of a job I was overqualified for. I could have worked there for a year or so, buying myself time to decide what to do, but in hindsight, I’m very glad I acted swiftly to avoid that path. It’s my belief that people “stuck” in jobs they hate are there because they haven’t practiced answering this question and acting upon it. This doesn’t always mean quitting your job, either. You can quit the idea of something before you officially quit it. Someone can look for opportunities outside of their current work (instead of quitting when they still need the paycheck).

Whether to quit, keep it the same, or double down is the big question for our career choices, relationships, personal or professional projects, and number of cats. It’s often thought about, but rarely answered, because it’s so easy to delay and so daunting to commit to. If the answer is delayed, life is also delayed, frustrating us and confusing our sense of life direction. Rather than wait until your hand is forced, what if you could skillfully and proactively decide what to do?

As I’ve said before, I almost quit blogging five or six times in the early days, simply because it was a lot of work and not much reward in terms of readers or money. Each of those times, I decided to continue onward. But one day, I decided to double down, and that’s been one of the best decisions I’ve ever made.

In 2012, I did marketing in different airports in the United States for Marriott. It was a fun, laid back job, but nothing of the career sort. In fact, it was a temporary job. When it was time to move to a new airport, I was told that our pay would be cut. After doing a great job, that didn’t feel right, so I decided to quit and swim back into unemployed waters (where I spent much of my post-college time). This was also about two years after I had started this blog. The blog hadn’t gone anywhere, but I wasn’t exactly working hard on it either.

This brought me to a big decision for the blog: quit, keep doing the same thing, or double down.

I had a little bit of money from my marketing job, I could still stay with my parents for a very low amount of rent (genetic discount), and my mom makes delicious chili. But I did eventually need to earn a living wage. Instead of throwing myself back into job applications, I decided to double down on this blog for one year and then reevaluate. Fast forward to today: It was a success and now I write books for a living. When I think about why I doubled down and why it was the right choice for me (even if it hadn’t worked out), there are four questions to consider.

Quit, Stay, or Double Down: Four Questions to Ask

Does it provide growth? Pain? Regression? Challenge? Does it make you a better and stronger person? The main reason I didn’t quit blogging sooner was right here. Blogging about personal growth had made me a better person. My writing improved. My self-discipline improved (slowly, and then rapidly once I found mini habits). My writing positively impacted other people even in those early days. So for such a failure from a business perspective, my blog was a tremendous success at the personal level, and I found great value in that. I may not have had the traffic of HuffPost, but I did have other reasons to keep writing. So I did. Doubling down on it was a way to see if I could make the business side work in addition to the personal benefits.

Analyze your cost of time, money, energy compared to potential gains. There are two factors to risk and reward. The obvious one is what you stand to lose vs what you stand to gain. This is incomplete, however, because it doesn’t include the probability of each. The lottery is pocket-change risk and you’re-rich-overnight reward, and that looks amazing until you find out that losing is nearly guaranteed. So when you think about what you’re risking in terms of time, money, and energy, and what you’re risking it for, also consider the probability of those scenarios happening.

You could have everything else in place, but if you have little to no chance to win, then doubling down could be a bad idea. That said, the chance for success in an area is tough to peg, so start by asking yourself if you’re willing to lose. With the lottery, losing is almost certain, but if you’re willing to lose $2, it’s not a big deal.

When I doubled down, my greatest risks were time and energy, because all of the time and energy I put into writing was could be used on my “traditional career path.” My college degree was also getting stale, which seemed to be an employment risk (“Why haven’t you used your degree?”). I didn’t know the probability of success, but the downside of losing time and energy to find out was well worth the chance to live my dream. I believed in my ability to figure out a career even if my writing attempt failed. My potential gain was the ability to write for a living, and so far, that has come to pass. With over 10,000 subscribers (it would be higher, but I remove those who don’t open my emails) and popular books that continue to sell in multiple languages, doubling down paid off.

Last week I went on a work cruise in Alaska and worked a lot on my upcoming book. This picture might be the epitome of the modern writing profession: wine, a laptop, and the sea… that’s all you need!

Opportunity cost is one of my favorite concepts in the world because it’s endlessly applicable and always a good question. Opportunity cost, or the cost of doing one thing instead of any other, is a part of the risk/reward analysis, but it’s rarely thought of in those terms. It’s important enough to be its own thing.

I’ll give you a current example of an opportunity cost I’m paying right now. One of my dreams is to write fiction, particularly interactive fiction, and expand interactive storytelling into audio and/or video and eventually into in-person experiences. Right now, I am NOT pursuing this dream (my website for this has been inactive). It’s a big chunk of the total opportunity cost of my nonfiction writing career, and it’s a cost I’m willing to pay at this time to help people change their behavior and see where I can go as a nonfiction author. That could change, or I could even try to juggle these two areas, so I periodically ask myself what is currently worth the cost of all other options. My answer today is the same as it was before I had succeeded: writing, researching, and thinking of creative solutions for lasting change is worth the opportunity cost of everything else.

Ask yourself: is what I’m doing now worth the opportunity cost of all other possibilities? If not, what might be?

The prior questions were logical. This last question is meant to draw out your gut reaction. Don’t overthink it. Do you like it and want to continue it, whether it’s your career, relationships, or a project? Feelings count, too, and they can often reveal hidden affinities or problems.

I’ve been wrestling with the decision to get a cat or not, and this question is what keeps me coming back to it. I love cats; my family always had cats; I can even speak cat — I make a cat meow so realistic that it tricks other cats and dogs (and one time, a tiger at the zoo). Logically, having a cat goes against some of the things I want, like complete freedom to travel the world. The counterargument is that I like to bury my face in their fur, watch them stalk things, or react to cucumbers. It’s a tough choice! Until I get more stability in my living situation (I’m a serial mover at this point, planning yet another move), I’m going to hold off on getting a cat.

Here’s a brief guide that puts all of these together.

When to Quit

  • When it takes more away from you than it gives you in return.
  • When the potential reward is no longer worth the risks and costs.
  • When you see a better opportunity.
  • When you don’t enjoy it. This is not as obvious as it seems, because when we do something for a long time, we may assume that we enjoy it, hiding our true feelings.

When to Stay the Course

  • When you’re uncertain about most or all of these factors.
  • When you need more time to decide. This is valid sometimes, but beware, as it is the most common invalid excuse. For example, I admit it’s possible I should have a cat right now.
  • When you need to see the results of an event before making a good decision (Will you get a raise? Will you have the opportunity to move somewhere else?)

When to Double Down

  • When it gives you more than it takes.
  • When the risk and reward scenario is agreeable. Consider the odds, and consider your life if you don’t succeed. The best ventures are still worth it!
  • When you believe it’s your best opportunity right now.
  • When you enjoy it overall, despite the difficulties.

Final Thought

Even with this analysis, there’s no rule. If people only played the odds and only made logical decisions, we’d have no superstars. With that, I must add one final suggestion of when to double down.

Double down when you simply want to take the shot and see if it goes in. Sometimes in life, you have to go for it. My “smartest play” was to go for a Finance job, but I wanted to take a shot at writing first. I knew I would wonder “what if” my whole life otherwise. What if I had really tried to make it as a writer? Since I did try, I have the answer: my first book would be translated into 14 languages. I’d never expect that, nor should I have expected it, but it shows that you won’t know until you try. The purpose of this article is to guide you toward something that’s worth trying and away from everything else.

Not everything is worth doubling down for, and in fact, more things are worth quitting, but in the end, it’s about doing your best to figure out which is which.

Stephen Guise is the author of three books, including the worldwide bestseller, Mini Habits, which is available in 17 languages. You can learn more about him here.


A network of business & tech podcasts designed to…


Written by


Stories & podcasts that make smart people smarter: www.Mission.org. The Mission Daily: www.apple.co/2KMXjhQ. The Story podcast: www.apple.co/2HEcveQ.


A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org


Written by


Stories & podcasts that make smart people smarter: www.Mission.org. The Mission Daily: www.apple.co/2KMXjhQ. The Story podcast: www.apple.co/2HEcveQ.


A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store