23. When to Quit Your Day Job
... if you want to
At the start of every product review on The New York Times Wirecutter website, the author explains why they are qualified to be telling you which Dyson hair dryer is best or what standing desk is worth the money. I wish there was an expert reviewer for career advice, too. But jobs are a bit more nuanced than appliances.
Nevertheless, people often seek out advice from others on when it’s time to jump to a different opportunity or start your own thing or flat-out resign to take some time to heal and rest. I have asked others for this advice. People have asked us.
Shannon and I recently shared our own career journeys of leaving jobs and starting Bonfire. Quitting a day job to start your own business is one end of the career-change spectrum, but we talk to plenty of others who wonder about leaving their current role to find their next role, somewhere the grass is greener (hopefully!).
Making the decision to leave – no matter where you’re headed next – is no easy choice. So in addition to all those helpful articles on the Internet about when to quit, here are some reflections I’ve found helpful to gain more confidence about whether it’s time for your next move.
How to know when it’s time to leave your job for your next adventure
1 - When you do not feel psychological safety
Psychological safety is a belief by your team that it’s okay to take risks and speak up and make mistakes without fear of any negative consequences. It creates a culture of honesty and trust and respect. It’s a great goal for any team to aspire toward; some teams are closer than others. But if you find yourself in a situation where any level of psychological safety seems untenable, then it might be time to move on.
Typically, some of the biggest warning signs or triggers that lead to toxic cultures are:
Injustice
Unethical behavior
Lack of attention to diversity, equity, inclusion
You’ll be the best judge of whether or not your team culture rises to a toxic level – and whether it’s temporary or permanent. Just beware the trap of unevidenced optimism where you think it might get better if you wait long enough because, I can tell you from personal experience, those wished-for good times almost never come and rarely ever stick.
2 - When your job is no longer serving your life
By now, you may have picked up on one of the central themes of this newsletter: Your life need not be in service of your work. Your work can be in service of your life.
For example, you may wish to run your own business some day, so you purposefully choose jobs that give you the experience of strategy, operations, and business development. Or you may want to have more time and space to work on a creative pursuit, so you look for jobs that pay well and don’t bleed into nights and weekends.
Recognizing your work as serving your life, rather than the other way around, can be a huge paradigm shift. For me, I fell into the muddy waters of overwork and work-as-identity the longer I spent in the corporate world. I needed help from good friends and great books to reframe what I was doing and why I was doing it. One of many “aha” moments came when I did a first session with a career coach who asked me, very plainly, what I wanted. My answer was something totally different from my current job.
Of course, this implies that you already know what you want out of life. Easier said than done! If you aren’t quite there yet, here are some ideas on how to navigate a quitting decision while simultaneously navigating a life direction.
You might not know what you want out of life, but you might have a clear idea of what you don’t want. This is enough to know whether your current job is a good fit.
Start the work of figuring out what you want out of life by taking baby steps. Ask yourself, “What do I want?” and listen to your real answer without judging it.
Take a simple exercise for understanding your personal positioning and how you want to show up in the world.
3 - When your job fails the Strength of the Workplace Survey
If you are anything like me, sometimes you just want to take a Buzzfeed-style quiz to tell you what to do next with your life. Well, good news. I have one for you!
Gallup, a global research company focused on the workplace and people management, studied over 100,000 teams to arrive at a methodology of measuring employee engagement. The results have been codified into their Q12 Survey, which measures the strength of a workplace.
The survey is a favorite one that I used with my teams in order to gauge how everyone was feeling. It’s super simple to run. It’s just 12 yes/no questions.
Gallup Q12 Survey
I know what is expected of me at work.
I have the materials and equipment I need to do my work right.
At work, I have the opportunity to do what I do best every day.
In the last seven days, I have received recognition or praise for doing good work.
My supervisor, or someone at work, seems to care about me as a person.
There is someone at work who encourages my development.
At work, my opinions seem to count.
The mission or purpose of my company makes me feel my job is important.
My associates or fellow employees are committed to doing quality work.
I have a best friend at work.
In the last six months, someone at work has talked to me about my progress.
This last year, I have had opportunities at work to learn and grow.
Ideally, people will be able to answer Yes to as many questions as possible. The more Yeses, the stronger the workplace.
But for the purposes of the quitting question, you can look at the inverse: Take the Q12 survey for yourself and count how many No answers you’ve come up with.
Pay particular attention to questions like:
At work, I have the opportunity to do what I do best every day.
My supervisor, or someone at work, seems to care about me as a person.
These types of questions touch on elements of the workplace that are much more immutable than others. It’s possible to make some tweaks so that you, say, have the equipment to do your work right (question number two). But it’s far harder to reconfigure your job so that you’re doing entirely different work or to rearrange your team and replace the people closest to you.
Also I’m aware that sometimes you just want a job, not a career. If this resonates with you, then go back to point #2 above and make sure that your job is serving your life and not the other way around.
Over to you
What have been your reasons for quitting in the past?
Are you wondering when to take the leap from your current role? (Let us know how we can help.)
What feels like the scariest part of leaving for your next thing?
Let us know in the comments or reply to this email. We’d love to hear from you.
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