I am having 3 or so career conversation requests coming my way via different channels every month. Sometimes I still feel a tiny bit junior to be doing this, but I do have faith that my advice is actually useful to some extent:
I recently realized I actually keep telling people some variants of the same four things. They’re not original to me at all, but collating them in one post seemed useful.
As many as you can (in terms of energy, resources, and availability)! Usually more people than you would expect are actually within your reach and willing to talk to you. Just ask.[1]
I was worried I would look stupid and would burn myself if I just had a casual chat with people. But I quickly realized that having a genuine chat was usually just the trick. Ask people about their interests, and talk about yours. It’s surprisingly frequent to find common interests where you would have never delved into in a structured conversation.
I also have a secret-not-so-secret list of questions that I like to draw from when in conversations, and they’ve been quite useful to have meaningful, interesting encounters. You can replace “work” or “job” with “life” or any container for parts of people’s lives:
And here I mean: probably more than what you are currently doing.[2] There are multiple reasons why applying to more things is good:
Also, you can just offer to volunteer. If one place is your dream place, give your time for free for a bit, and maybe you’ll see that there’s actually nice place to be carved out for yourself there, and prove that you fit right in without involving to much effort on their end.
Lay your thoughts out on a Google Doc, and find trusted and critical people to review them.[3]
It's generally a good practice to explain your thinking, understand your considerations better, weigh the pros and cons, identify your uncertainties and your needs.
Depending on how important it is, layer the feedback:
It’s useful to get 3+ feedbacks at least, because you might overupdate on 1-2. You want the trends, not the hot takes that might not actually make sense in your specific context.
You might also want to get feedback on yourself (here is a template I made if you want one) - but you need to be in the right place and ready for what you might read.
I first learned about this during the recruitment process for Charity Entrepreneurship where they ask you to perform this analysis for your different career options, and I have been using this quite regularly ever since, especially when I feel stuck in a decision I want to make (career-wise or not!).
It’s a good exercise to reflect on what you value (criteria) and to what extent (weights), and to figure out the good and not-so-good questions to trigger the right introspections and useful emotions to help you make decisions. Then put numbers on all that. You shouldn’t take the result at face value: this is just a model, and as any model, it can’t comprehensively represent what you’re trying to model. But it’s a good starting point.
You can also seek feedback on your scoring, though it’s usually a bit harder to read for other people.
I have developed my own WFM template, so feel free to make a copy and use it! There’s one tab specifically for career decisions, with more detailed questions and weights that you can adjust to your own preferences, and a tab with just the formulas.
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I hope this can be as useful to others as it has been for me over the years. I’d be happy to hear about other systems people use and compare!