Speed Date Your Future Career Path

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Exploring a potential career transition can feel squishy and overwhelming. Bringing a bit of lightness to the process can help transform your career exploration from one of paralysis and heaviness to doable and – dare I say – energizing. Borrowing the speed dating framework can help with this.

The traditional speed dating process involves singles gathering together to progress through a set of brief conversations, each held without commitment, to explore the level of intuitive fit with a potential love match. Then, where folks have hit it off, they are free to pursue further contact.

Applying this framework to the career exploration process requires a few simple modifications. Here is what the career speed dating process looks like:

  1. Draft targeted questions based on your non-negotiables
  2. Assemble a group of potential career matches
  3. Conduct a quick intuitive assessment of potential fit and priority
  4. Hold short conversations to try on each top choice
  5. Reflect on each conversation to refine degree of potential fit
  6. Pursue additional exploration with paths of interest

Every powerful career or job transformation starts with getting clear about what is important to you and the rubric you will use for evaluating and recognizing your next career move. Distilling your prioritized criteria for what you want includes an inventory of your values, your favorite skills, your personality, your ideal work environment, what you find satisfying about your work, what job duties you want to include in your charter, your compensation package, and several other qualities. The more you can get clear on what is important to you before you start speed dating, the better. 

Drafting questions that are open-ended in nature (starting with what, how or explain…) and focus on what you know is important to you ensures any speed dating conversations you have will be about criteria that truly make a difference for you and will help you follow your energy. Though it is tempting to skip the question crafting step, it is essential because it makes sure you are talking about things that matter to you.

Determining your potential career matches is a combination of examining the options you have embraced and considered in the past, brainstorming new ones, and learning from hiring and employment trends based on how the world is evolving. Coming up with an initial list of options you have the most energy for is a good start. If this feels hard, there are several assessments and online databases and research that can help you find an initial toehold on options to consider; you can also work with a career coach to help you navigate this step.

Running these options through a quick intuitive assessment of the likely degree of fit against what is important to you will give you a head-start on the areas you need to examine most for each one. Make sure to not get ahead of yourself, writing off an option because it does not feel practical; rather, use what your intuition tells you as a guide for what to double down on in the question to check your assumptions.

Holding short conversations with those in a position to help you requires finding people in roles that are relevant to those you are considering. Asking for a short conversation that you have prepared well for is something that you may resist doing but that pays incredible dividends. Find people in your network and those in your close connections’ networks to draw from, and consider holding 2-3 conversations per field you are considering to gain a well-rounded view. You may need to ask more people than you ultimately speak to, as not everyone will say yes, but more will than you think.

After each conversation, reflect on what you learned and revisit your non-negotiables to refine the degree of potential fit. Follow your energy to pursue additional exploration with the paths that show the most promise for you. Promise includes your natural degree of enthusiasm when you consider the career option as well as what feels like you can see a path forward to. Don’t be afraid to hold options that feel a bit out of reach; you would be surprised how a longer-term strategy to a career pivot can get you there, and/or how other options that are related to the target directions you are drawn to can involve a less steep transition curve to acquire.