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A simple guide to definitively answer whether or not you should quit your job

A Microsoft and Amazon alum, Neima Shahidy admits jobs aren’t going to be perfect all the time, but you need to make sure you’re staying or going for the right reasons.

A simple guide to definitively answer whether or not you should quit your job
[Photo: Klaus Vedfelt/Getty Images]

Job openings neared a record high at the end of last year and employers are still struggling to fill positions. Getting hit up by a never-ending deluge of recruiter emails and contending with the fear that you’re growing slower or earning less than your peers can cause a lot of anxiety. Or maybe you’re worried that the phone isn’t ringing as you read headlines about everyone else getting pay increases or promotions. In any case, asking for what you want can cause a lot of anxiety. And moving jobs can cause a lot of stress.  

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I’ve been there, and I know how paralyzing it can be to feel like you’re on a trip without a map.  

I love my job as vice president of product at Jerry. But I didn’t always expect to get here. Early in my career, I bounced between regulatory affairs, brand management and various marketing roles. I got my big breaks at Microsoft and Amazon and found my next hyper growth opportunity at Jerry. Along the way I developed some principles to get a job that positions you for both success and satisfaction.  

Shop for job opportunities the way you shop for a house

Some people are looking for a short commute to work, others want to live in a walkable neighborhood. Just like priorities for a house hunt, get clear on priorities for your next job with “this vs. that” thinking. Write down the things that are the most important to you, and use them as a compass. Evaluate every opportunity on whether or not it gets you closer to what you want. If it doesn’t, filter it out.  

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Early in my career, I knew I valued working in a fast paced environment and it was important to me to break into tech. So I focused on the quality of the company and the quality of training experiences more than the domain or function. I joined Microsoft in Channel Marketing focused on the mice and keyboards business. I was willing to take my second or third choice function because I knew I liked working in tech and, when I looked at the careers of people that worked there, I recognized it was a great place to launch a career.  

I stack ranked company quality and training over job function or domain. I found myself doing this again when I wanted to increase risk in ownership. I focused less on domain. For example, I didn’t have a predetermined passion for insurance, which is what my current company was focused on when I joined. But, I am passionate about how technology could make daily tasks better and I wanted to pick a great company that would let me take on more risk. 

Focus on trajectory

People tend to focus on the tangibles: compensation, company, and title. While these factors aren’t negligible, ultimately you work with people, and they tend to have the biggest impact on your overall career trajectory. People who teach you a lot and help you be your best act as multipliers on your career trajectory. 

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Throughout the courting process with your future employer, ask yourself these questions:

  • Of the people I spoke to, have they treated me with respect? 
  • Do they have skin in the game and do they have a track record of growing people like me?
  • Do I get the sense that I can learn a ton from them?

Focus on putting yourself in positions where these are true. 

For example, I was contemplating moving to Seattle for a new role at Microsoft on the Surface team. The job description didn’t exactly meet my list of priorities, but when I met with the team, it was a no brainer. Each person I spoke with had so much passion for the business. I knew I would learn working alongside them, and it was clear they were invested in my personal growth.

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If you’re feeling drained, do something about it

It’s important to be resilient during challenging times at any job in order to achieve mastery and maximize your impact. But if you feel like your job drains you for weeks at a time, the first step is to look inward.

  • Has something changed about you or your priorities?  

The second step is to look at the job.

  • Did something change about the role or is it materially different from what you expected?

There are people that leave at the first sign of trouble, and people that stay too long. Don’t be either. 

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In my last job at Amazon, I realized I was feeling drained. To a lot of people, the role I had was a dream job, but I wasn’t learning at the pace I wanted to. I realized that what changed was me. It was time for me to take bigger risks with my career versus continuing to work at a company that was already quite successful and offered stability and a clearly paved path. While stability was something that was important to me early on, I realized that my new priority was to build a successful company versus working at one that’s already there. 

Jobs aren’t going to be perfect all the time. But if you’re in a job that isn’t making you happy for an extended period of time, you have options. Go do something about it.  


Neima Shahidy is vice president of Product & Partnerships at Jerry.

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