Questions to Help You Decide Whether to Stay or Leave a Job

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Originally published at https://www.thrivecoaching.io.

“If I had an hour to solve a problem I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.” — Albert Einstein

Part of understanding the problem is making sure you’re asking the right questions.

Unfortunately, we’re not taught in school how to ask ourselves better questions. Our natural inclination is to ask “why” questions like “why me” which send us into a downward spiral.

But when we change our questions, we change our lives.

By asking better quality questions, we gain better quality insights that can lead to powerful transformations.

Below are a series of questions I gathered from my coaching courses and friends, I found online, and I created over the past five years to identify my vision for my career and determine if I should stay or leave a job or organization.

Spend time reflecting and journaling on all or some of the questions below.

First, see if it’s the role, company, or you:

  • When I look at the opportunities ahead of me at my job, how do I feel?
  • When was the last time I woke up excited or feeling optimistic about the role/company? What happened right after that?
  • What specifically about my current situation is frustrating me?
  • What would it take for me to be happy at my current job? What would make me want to stay?
  • What problems do I expect quitting my job to solve? Will these show up in a different company? How might addressing these now benefit me?
  • Have I taken every action possible to make my current job workable?
  • Where am I not being honest with myself?
  • Am I still excited about my work — or am I holding onto this job because it’s what I’m used to, because it’s what I thought I wanted to do, or because I’m afraid to make a change? Or is it the person I used to be, and now I am growing into something and someone different?
  • Am I running away from something or toward something?
  • Where am I being too flexible? Too rigid?
  • Are there other roles, opportunities, projects, or clients I could work on at my current job that are interesting to me — or not?
  • Where does my current employer share similar values (e.g., growth, learning, contribution) that are most important to me? Where are our values misaligned?
  • If my boss fired me right now, what would my reaction be?
  • What’s making this decision particularly difficult for me right now?

Tap into your heart, values, & dreams a bit:

  • Am I burnt out and would taking time for self-care, vacation, or getting help with stress solve the issue?
  • What are my strengths? How am I using them in my current role? How could I increase how much I’m using them?
  • Do I want to do this (role/company) for the next five years? Thinking this far ahead, what do I notice happens inside my body?
  • If there were no consequences, what would I do?
  • What was the original vision when I started my career? How has it changed? What aspects of my current job directly relate to my vision?
  • What do I want for my job, career, and life? What do I really want?
  • Where does my work currently align with my greater interests, passions, and goals in life? Where is it not aligned?
  • What do I want my life to look like in five years? What do I want to be doing in five years? What part of that could I be doing right now? How can I plan and prepare so that I can be in that position in five years?
  • If I could do what I do best consistently, what might be possible?
  • If I was more willing to step outside of my comfort zone, what opportunities would arise for me?
  • What would I pursue if I knew I couldn’t fail?

Tap into your head & reasoning a bit:

  • Can I defend my choice to leave, even if others disagree with it?
  • Do I have a thoughtful, realistic plan for attaining my next job?
  • Am I willing and able to forego benefits like health insurance and retirement contributions until I get my next job?
  • Do I have the support of my family and friends? Do I need it?

Integrating your learning:

  • What’s emerging here for me? What new connections am I making?
  • What’s been my major insight/discovery so far?
  • If there was one thing that hasn’t been addressed to reach a deeper level of clarity, what would it be?
  • What are my next steps?

I hope these questions act as a catalyst for you and uncover insights you might not have had previously. If, in the end, you decide it’s time to go, exit with grace and gratitude for this chapter of your life and all of the learnings it provided.

Additional resources

  • Course: “Should I stay or leave” by Career Coach Darcy Eikenberg. This course and Darcy’s coaching were instrumental to me when I was first deciding whether to leave a prior organization.
  • Book: Designing Your Life by Bill Burnett and Dave Evans
  • Career or life coaching! You can learn more about the power of coaching here.

Special thanks

Big thanks to Robbie Abed, Erin Van Der Meer for some of the questions provided, my friend Stephanie Ciccone-Nascimento for the inspiration to think bigger, and thanks to my personal coach Julia Tolstunova for holding space for me and championing me.

30-Day Earth Challenge

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How fast do these things biodegrade if left in the environment?

Vegetables? 5 days – 1 month
Paper? 2–5 months
Orange peels? 6 months
Tin cans? 50–100 years
Styrofoam cups? 500 years to forever
Plastic bags? 500 years to forever

500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever 500 years to forever

When I stop for a moment and think about how much plastic I use regularly because of laziness and inconvenience, I don’t know about you, but I experience deep shame.

About five years ago, I first learned about the Great Pacific Garbage Patch from a friend and colleague, Lindsay Thibeault.

I’d never heard of it before.

If you haven’t heard of it before, it’s a garbage patch full of plastics and trash in the North Pacific Ocean. It’s said to be TWICE the size of Texas. The patch is also believed to have increased “10-fold each decade” since 1945, and it’s estimated that by 2050, there could be as much plastic, as there are fish, in the ocean.

I remember thinking, holy cow, how have I never heard of this before? How could I be so careless (I was using AT LEAST 2 new plastic cups at work every day)? How could it be possible to deny the impact humans have on the planet when we look around? And worse of all, how could I stand by and do nothing?

To say plastic pollution is a widespread problem is not doing it justice:


We have done small things in our house here and there to try and make a difference: go veggie, remove plastic straws, remove plastic storage containers, stop buying from Amazon, always run full loads of laundry, buy less things/clothes, educate ourselves — BUT there’s more we can be doing.

That’s why I’m dedicating this month’s 30-Day Challenge to Mother Earth.

It’s so fitting, too, considering April 22 is Earth Day!

I put together this 30-day challenge for any of those who want to participate. If you can’t do it all, that’s okay; even doing just a few of the items will make a difference!

Here’s the 30-Day Earth Challenge:

It’s also linked here.

These next 30-days are coming whether we want them to or not, why not do something wonderful for the earth. Who’s with me?

Marketing to HR: The Best Newsletters, Content Syndications, Slack Communities and Podcasts to Fuel Your Marketing

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If you’re new to HR marketing/sales, then you know there’s a lot to learn. This is especially true for the majority of us who weren’t in HR or people Operations before.

An excellent way to learn about the function is to immerse yourself in their world. One way I made the transition from marketing to marketers at HubSpot to marketing to HR was to sign up for the most popular content that people operations professionals are learning from. This not only gives you insight into what’s going for them, but it keeps you abreast of the most essential HR news, trends, topics, data, and more. These insights fuel your marketing, your messaging, your positioning, your content, your conversations — everything you do.

Below is a list of suggested content that I encourage every new team member at Compt to sign up for/subscribe to when joining our team.

NOTE: This list is by no means comprehensive, but if you see something I should add, send me a message on Twitter (@sbedrick). And if you’d like to join the People Ops marketers slack I created filled with folks from Lola, Employee Cycle, Robin, LearnLux, Humanyze and more — ping me on Twitter.

HR/POPs Newsletters:

Content syndications:

HR Slack communities:

HR Podcasts: