Planning an upward career move? Here are 4 strategies I learned while job seeking

Credit: Ilana Guttman

Ready to leave your job for greener pastures, and not sure how to start? Hi, I’m so glad you called/wrote/stopped by.

And who am I? Not a career counselor or advisor; just a motivated, career-oriented Joe like you. More and more I have friends, former colleagues and 2nd-degree acquaintances asking me how I thought about my job search process, career stepping stones, choices I’ve made.

There’s nothing like some hard-earned life experience — filled with self-discoveries, rookie mistakes and surprising outcomes — to semi-qualify me for jotting down what I find myself (enthusiastically) repeating. Based on my recent experience, I present my ‘career move learnings’, in four phases.

Phase 1: Identify your professional core values

While considering leaving my last job I spent a lot of time juggling and putting weight behind my ‘priorities’ for a next career move. Work life balance? Better salary? Interesting sector? Good management team? Etc… But I found myself stressing that ALL are equally important and building up an idea of a perfect job, which in turn paralyzed me from having faith I could find something I could actually be happy with. Which demotivated me as I solidified the assumption that I’d never find the perfect job, so why bother looking.

That changed when I started breaking it down differently. After working on a corporate core values project, I realized I needed to identify my own ‘core values’ — in life, in light of what the pandemic had done to shake up my life, and professionally. I started outlining my ‘professional core values’: the things that I consider central to who I am professionally and constructive for getting me where I want to go next. Examples:

…those are some personal examples, but there are tons more you may identify with. Once I outlined what I am looking for in that framework, I found myself breathing easier.

  • I could accept that chances are, I will find most and not all of these things in a specific job, while aiming to someday achieve each at some point throughout my entire career.
  • I could find like-minded people to relate to and ask for advice.
  • I could give opportunities a chance that I may not have looked at otherwise.
  • I could rule out job descriptions or cut short interview processes that were not leading me towards living my values.

By the way — our core values are actually already in us, identified by us, but perhaps not organized so succinctly yet. There are core values in my marriage, between me and my partner. My family is ingrained with core values. Your current company has core values — and they may or may not align with yours. The empowering piece is calling them out, naming them, and identifying which are truly essential for your personal career wellbeing.

Phase 2: Interview yourself

Open a google doc or take out a piece of paper and start mapping out some characteristics about yourself to get to know yourself a little better. Literally: Interview yourself.

  1. What did you love the most about your last two jobs?
  2. What did you like the least about them?
  3. If you can only choose 3 top priorities for your next workplace, which would they be: upward mobility, learning opportunities, high salary, flexible hours, great team, good brand name, established corporate atmosphere, bootstrap startup atmosphere, product/cause you can throw passion at, etc.
  4. What are your deal breakers? (ie, ‘’it is a deal breaker for me to not have a work from home option’’ or ‘’I must be able to pick up my kids by four’’)
  5. Consider what kind of job you want after this next one — where do you feel you’re headed? Where do you want to end up? Then it’s easier to work backwards — how do you get there?

Bonus exercise: Make your own job description

When you have some answers, go to LinkedIn or Glassdoor and look at job descriptions — which aspects of them excite you? Even if they are impractical (faraway location, too senior/junior) — just notice which excite you, get a sense of which titles are worth aiming towards. Then, write your own job description — piece together what you liked, Frankenstein it up. It serves as a central compass for what your gut is telling you to go for and how you want to grow in your next career move.

Phase 3: Come to interviews equipped — with your own due diligence process

This may take having a few jobs under your belt to really absorb but there’s no reason not be smart about this early on. A hiring process is always two ways — they’re interviewing you but you’re also interviewing them (and the degree varies at different stages of the process; the later you get, the more ‘real’ the answers will seem). It’s just a matter of actually recognizing that you have the power to ‘due diligence’ your future workplace.

  1. Come to interviews with prepared questions that will paint an idea of where you’d be working. What is the team culture like? What inspired you to join/start this company? How do conflicts here get resolved? How do you celebrate wins?
  2. Ask questions that reveal expectations about your specific job. What should I have accomplished in the first 3 months and 6 months? What will you look for to know I am succeeding? What is your communication style?
  3. Find mutual, trustworthy acquaintances to ask about the people in management or members of your future team. Are they work/life balance oriented? Are they ambitious and motivated? Are they able to get light and have fun on the job?

Phase 4: Getting close? Talk it out

Finally, have this arrow in your quiver — trusted mentors or advisors or past colleagues or others who know you with whom you can reflect, go over your pros and cons, and listen alongside as you hear yourself speak. Do it with more than one or two people. Your gut feeling will reveal itself easier when you express your thoughts and concerns out loud, a few times, until — like in my case — you’re practically hoarse by the end of it.

Good luck out there. It takes a lot of guts, ambition, and clarity to go through this really intensive, often exciting, often painful, process. But what many people miss is the self awareness required. Listen to yourself, give yourself a chance to really be mindful of who you want to be in your career and how to leverage who you are to get there.

I want to thank a long list of people across my life who have supported me, gave me guidance, and contributed to these tips through their generosity of time, experience and attention. From the words of wisdom to the professional advice to the friendly ear, all contributed to my figuring out what I truly want and even moreso, how to stick it out until I got it. I hope with this article I have offered you the same.

Taking notes. I’m curious. Hetz Ventures. 50:50 Startups. I write insightful articles with career, marketing themes. And personal topics at

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