When is it Time to Leave Your Job?
Do we ever really know when it’s time to leave a job and start something new?
Maybe you get laid off, or the start-up you are working for is clearly headed for bankruptcy. Maybe you fall in love with someone while on an international whirlwind trip and decide to reframe your entire life and start anew. Maybe you’ve slept at your desk for the past 3 nights, with only short breaks to race home, brush your teeth, and then head back into the office. Or you spontaneously shed a few tears from physical and emotional exhaustion in a cab home from the office <that was a clear reason for me to quit a previous investment banking job in my 20’s>.
There are times when leaving is just…obvious.
But for many people and in many circumstances, leaving a job is an extremely difficult, bittersweet and handwavy decision. It could go either way. You waffle, fret, use your therapist -and all your friends as pseudo-therapists- to make your decision.
I knew it was time to leave a recent role when I quit...for the 3rd time. Third time's the charm, they say. But in my personal journey, and in mentoring and coaching others in their journeys, in navigating the question of “Should I leave my job?”, I’ve amassed many helpful perspectives and approaches in this decision making process.
The following advice focuses on getting extremely clear about your current situation. It doesn’t dive into evaluation tips for “this job” vs. “a new offer”. My decision was between staying in my role, or leaving to take time off, not leaving for another role. After 12 years at the same company, I wanted a substantial “self-imposed sabbatical”.
That said, too often I’ve seen folks jump to take shiny offers at new companies later to realize that the new role or the new company has its own set of similar-but-different problems. Before you think about leaving for something new, first get clear on the “now”.
If you’re reading this -you either know me, or you are thinking about leaving your job.
Sending you clear, confident, and collected vibes if it’s the latter!
Much Love, Beck
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First off, Guidelines
Below are a few ground rules that are VERY valuable for anyone thinking through the question: “Should I leave my job?”.
Rule #1: Be in or get out. Don’t be the person who constantly thinks about leaving a company… It’s not good for you, it’s not good for your team, and it’s not good for your friends and family. Allow yourself to “check-in” on things every 6 months. If, in that check-in, you decide to stay, then stay. No recruiter calls. Not even coffee dates to casually explore new opportunities. Commit. Obviously if shit seriously blows up, that’s grounds for you to break this rule…but on the whole, it’s helpful to stay focused.
Rule #2: Be intentional about “What needs to be true for me to stay?”. Imagine 6 months to 1 year from now. What elements of the company vision, your individual role / opportunity, and your lifestyle boundaries need to be true? Lifestyle boundaries are elements like the number of hours worked per week, the amount of travel required, commute time, work from home ability, general work flexibility, etc. Write these answers down! Seriously, write out a vision of the future you want... and email it to yourself. Having this private and written manifesto allows you, in the every 6-month check-in, to evaluate your reality vs. your earlier vision. If you are a manager, it's critical to deeply understand how all of your direct reports would uniquely answer this same question. I've made the mistake of imposing my own values and assumptions on folks on my team, which meant I lacked a true understanding of their values and needs. This major misstep led to offering poor guidance when helping employees think through their decision.
Rule #3: Be grateful for your current experience. If you’re in the “grey zone” -not the “get me out of here zone”- for the decision to stay or go, then there’s at least some value in your current role or at your current company. Be thankful for this experience. Holding this mindset helps you follow rule #1, as it’s possible to be fully committed when you are grateful for what you have.
Next, Pick Your Evaluation Approach(es)
Now that you (1) only think about leaving once every 6 months and (2) have a clear vision of “What needs to be true” for you to stay, you can select from one or many of these various approaches to help you make the best decision. The goal is to make your choice from a point of clarity, not from (solely) emotion.
The Pro vs. Con List
A basic framework that works. Write down all the pros of your job -eg. you love your manager, you love your team, you have a short commute, you’re inspired by the company’s mission, most days you come home feeling energized, etc. Note, if this is what your pro list looks like -you should probably stay put :) Similarly, write all of the cons -eg. you work too many hours per week, your boss is a micromanager even after receiving feedback, you’re on a project you don’t enjoy and aren’t learning from and you can’t see a path forward, etc. There’s no magic answer when using this framework, but laying out the information visually helps to make a holistic decision.
The pro/con list, in itself, is valuable even if you stay in your role. You can easily identify pros that are unique to your current role or company and difficult to replicate elsewhere vs. pros that you can find elsewhere. Similarly, you can look at cons that are unique to your current role / company vs. cons that are more universal. Identify where you have agency to enact change. For example, if you are working more hours than you want, ask yourself“Why am I working this much, and can I change my situation?”. Perhaps conversations with your manager, or stronger personal boundaries, will enable you to remove some of the cons on your list.
The Portfolio Evaluation
People, Product, Process & Package [And Culture]
Below is a more robust set of questions to help you evaluate your job. Think of it as a personal Net Promoter Score (NPS) survey for your job and company. Answering these questions -and analyzing the results- gives you an improved picture of your entire work experience. Do you have high scores in certain areas and weak ones in others? Are there possible areas you can drill down on to improve with your manager, peers or team?
People - On a scale of 0 to 10
Do you respect, value and learn from the people you work with?
Do you do you respect, value and learn from your manager?
Do you work in a safe and collaborative environment?
Product - On a scale of 0 to 10
Do you love the product you work on?
Does the product your company creates bring you or others joy?
How proud are you of the product’s mission?
(You, in the) Process - On a scale of 0 to 10
How impactful can you be within the organization in your current role?
Do you use your skills every day?
Are you learning?
If you identify process gaps, do you have agency to fix them?
Do you have a clear picture of your future career path within your organization?
Package - On a scale of 0 to 10
How satisfied are you with your compensation package?
It’s critical to reflect on your whole package. This is everything from financial compensation including base pay, bonus, equity or options, benefits…to less tangible compensation like commute time, time off allocation, schedule flexibility, trainings, etc. I’ve seen employees leave roles for more money, without fully accounting for the less tangible things like commute time, work/life flexibility, etc. Money is important -and it’s important to feel fairly financially compensated for your work. But chasing the highest bidder is rarely the right choice unless you have very specific and time-boxed financial goals that are more important to you that quality of life -ex. make and save $X over the next 1-3 years to invest in a downpayment for a house, have a college fund of $X for my kids, go back to MBA/PHD program, change industry / career, leave the bay area, etc.
Culture
For me, culture is queen (or king).
Culture is an ambiguous term used to describe “the essence” of a company. But ultimately, culture is the tangible output of a company’s values and how they manifest day-to-day in the work experience. Culture is comprised of the beliefs, attitudes, behaviors and systems of individuals and teams. It’s largely influenced, but not dictated, by leadership. Culture is the sum of the people, and how they work together.
Companies publish their aspirational culture though methods such as internal “company employee or leadership principles”, or though mantras. For example, early Facebook had a mantra of “Move Fast and Break Things” to encourage speed of innovation, even at the cost of stability. Amazon has 14 leadership principles, including "Customer Obsession", and a unique one, “Frugality”, which encourages leaders to be cost conscious with everything they do.
There’s often truth to a company's aspirational culture, but there are also disconnects. Get clear on both -Are you inspired to work at your company’s aspirational culture? What about the current realized culture?
Below are key free form questions to ask yourself around company culture.
What key values, principles, behaviors and systems define the culture of your company, or your organization?
If your company has published people operating or leadership principles -how closely do the day-to-day actions of people, or teams, in your organization match those principles? Write examples.
What are the actions of leadership that reinforce, or contradict, the ascribed company culture? Write examples.
What personal stories do you have that exemplify the culture? Are these stories unique, or could you imagine that same story at many other companies?
Do the values and principles align closely with your own values / strengths?
On a scale of 0-10. How would you grade your company culture?
The Long Game
Are you excited about (and believe in) the 3-5 year vision of the company? This is a simple yes or no question that can be paired with other approaches.
If yes, great! Add a “gold star” to some element of your other approaches to capture this win.
If no, then you may want to lower your scores from the portfolio evaluation. Or if your pro-con list hasn’t taken a forward-looking stance, make sure to note your “no” answer as a “con”.
Answering the long game question helps you get clear about your time horizon in looking for your next job. Perhaps you’re excited about your current 6-month project, but not excited about the longer-term. With this information, you may want to start your search right before your project wraps up.
The Immediate Game
Look back over your work calendar for the past week or past month. Go through your days -mark time slots in green for “good”, meaning it was a good meeting or time slot where you were productive and valued, yellow for “neutral” and red for “bad”. Think about your evenings and weekends, too. How much of your weekend was consumed with work -either actually doing work product, or stress/worry about work?
Check in with your community. Ask your partner, close friends, and family -How has my energy been lately? Am I more, less, or equally focused on work? Do you have examples of how my work -positively or negatively- is impacting our lives?
Then answer the following questions:
How were your days on a scale of 0-10?
What rough % was “good” vs. “neutral” vs. “bad”?
Similar to the “long game” approach, you can use the “immediate game” info to sway your decision. For example: if your days are largely “bad”, identify why. Is there anything you can do to shift off of a problematic project, or solve/move away from a problem? Alternately, if most of your days are good, or many chucks of your days are good, but you are concerned about the future…it might be worth staying another 6+ months to enjoy the day-to-day before looking for your next opportunity.
Don’t Just Resign! First Talk to Your Manager
Part of the reason I “quit 3 times” was because each time I raised concerns, my manager and I had valuable conversations that helped uncover, shift and minimize issues. In our conversations, with his help, I was able to negotiate new agreements around responsibility that better aligned with my passion areas. Ultimately there wasn’t a way for us to flex the long-term solution to work for me. But these early and often conversations helped the two of us connect on what was important to me, and therefore illuminated how I could better help the company. There is often a “there there” available -where you get what you want, and the company gets what it needs.
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If you do decided to resign from your role and leave your company, check out my post around Lame Duck Status -Leaving the Company Better Off Than When You Found It. Remember that last impressions are often the most important impressions.
And if you’re privileged enough to take time off between roles, check out my post Taking a Break: a User Guide for Time Off From Work.