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Parallels Between Dating and Your Career

Rachel Serwetz
Rachel Serwetz
June 9, 2020
Parallels Between Dating and Your Career

There are various intriguing similarities between dating and your career in terms of the process, your mindset, approach, as well as how it impacts your life more broadly. First, let’s think about the stages of the process.

Learn what you want first

With time, you learn more about what you want, but there are ways to learn about what you want BEFORE you get into your next “relationship.” The more you figure out what you want, the easier it is to narrow your search, assess options, accept sacrifices that aren’t crucial, and confidently identify when you found something that fits. In order to figure out our ideal career path, it takes learning about ourselves and simultaneously learning about what’s out there until you feel clarity on what is right for you.

Strategic Searching

When you’re drowning in the job search engine “black hole” it’s like spending hours blindly “swiping” on dating apps (versus doing something more strategic and worthwhile to improve your odds of finding the right match). Reflect on the most strategic use of your time versus doing things that are transactional and may not produce results.

Interviews are Dates

Don’t forget that interviews are a TWO-way conversation to get to know if it will be a good fit. It is not something “transactional” to solely win them over, but also to make sure it’s right for you, too. Notice how you feel when you’re in the early days of learning more about an “opportunity.” You should enjoy these and treat them as a conversation versus a one-sided assessment. It’s helpful to figure out what “job” you want by thinking about what conversations do you want to have? With whom? About what? Also, notice how you feel during the interview (date) to signal your overall feelings; if the interview isn’t genuinely enjoyable, the job likely won’t be either.

Figuring out when it’s time to leave

Often you’ll doubt if the current experience is still right for you. Having done your upfront due diligence to figure out what’s right for you, it’ll make it much easier to know whether the experience is stacking up against your standards, goals, or potential. Knowing when to leave is often a gut feeling. If you’re really not sure, write down all of the things you want and deserve and then assess the current situation against that. The grass will always seem greener, but if you don’t have your standards in place, you won’t know whether to be grateful and ignore your natural human curiosity, or whether it truly is time to move on.

If you decide to leave, you’re the breaker upper

It’s very hard to do this and we often wait way too long to muster up the courage to do so. Find support (not validation) from others, and find the courage within yourself to do what you know is right versus wasting more of your own time, and theirs.

If it’s not your choice to leave

You’ve been broken up with. Similarly, you need to mentally process and digest this before you head into your next “search.“ You need to feel confident, ready, and excited to be able to find and secure a next step that is right for you. (Personally, when I left a company and felt like an ultimate failure, I was at an all-time low and resorted to a toxic relationship as a distraction. I also was actively avoiding pursuing what was right for me because I was scared shitless of entrepreneurship!)

The mindsets are similar too

  • We often operate out of the wrong mindsets when job searching (and dating) — i.e. 1) wanting a sense of security (checking the box, just having something), 2) being too open instead of targeted in our search, 3) focusing on swiping instead of being strategic, 4) looking at others’ success versus our own (keeping our eye on our own paper), and 5) operating out of fear. Know what’s “driving” your decisions and actions, as it will directly impact your outcomes.
  • Use intention + intuition to make decisions — When you ask yourself if you’re making the right decision or not, use and don’t avoid your gut. This is how we operate in alignment with the universe versus self-sabotaging and making decisions we know are wrong for us because we’re scared to face what’s right.
  • It takes time — Effective and thorough career exploration (and job search) require patience and persistence (as does dating). With one job (or relationship), you’ll get closer to what you want but you’ll learn about what you don’t. You’ll leverage this in the next search. Your goal is to do as much ‘in-between’ research and self-reflection to get as close as you can in the next time around to making the right decisions and finding the right opportunities.
  • Tolerating uncertainty is the key here. As humans, we don’t like to deal with uncertainty. First, acknowledge that the process will take time and that it might be a ‘winding road’ towards achieving your ideal outcome to help you feel more comfortable pursuing (and maybe enjoying) the journey.
  • Be honest about admitting you’re not sure what you want and spend the time to figure that out before you “search.”

Why this all matters

  • Your success and wealth accumulation is directly tied to your job satisfaction
  • Job fulfillment and job engagement affects your personal life, your wellbeing, your mindset, your choices, your relationships.
  • Having clarity and confidence about your purpose is a huge sense of relief and excitement to pursue the path and the life you were meant to!
Parallels Between Dating and Your Career

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Rachel Serwetz’ early professional experience was at Goldman Sachs in Operations and at Bridgewater Associates in HR. From there, she was trained as a coach at NYU and became a certified coach through the International Coach Federation. After this, she worked in HR Research at Aon Hewitt and attained her Technology MBA at NYU Stern. Throughout her career, she has helped hundreds of professionals with career exploration and for the past 4.5+ years she has been building her company, WOKEN, which is an online career exploration platform to coach professionals through the process of clarifying their ideal job and career path. She is also an Adjunct Professor of Entrepreneurship at Binghamton University and has served as a Career Coach through the Flatiron School, Columbia University, WeWork, and Project Activate.

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