10 Tips on Navigating Career Transitions

You might find yourself in a moment in your career when you are thinking of what’s next. That’s an interesting twilight zone: you feel like you ready to give up old, but not sure what the new is. That’s where I found myself not so long ago.

I believe career decisions are very personal — and I doubt all ‘one-size-fits-all-your-parachute-color’ approaches. However, there are great thought partners who can inspire and create some support. You can find them among friends, mentors, or inspiring strangers who spent weeks and months figuring out similar things. Here are some ideas that can help frame and navigate your thinking.

1. Amazing long-read piece by Tim Urban of Wait But Why: How to Pick a Career (That Actually Fits You). Tim has a great way to explain and narrate things, and he’s spot on about how we are oblivious about many aspects of our career choices. https://waitbutwhy.com/2018/04/picking-career.html
2. Can Newport’s So Good They Can’t Ignore You is an amazing amazing book. Cal is a super nerdy Computer Science professor and MIT grad. He is also curious about productivity and decision making patterns that humans fall into. He introduces the idea of rarity and value as a part of career growth. When someone asks me about their professional development or jumping ships, that’s the first book I recommend. https://is.gd/69bItc
3. Ikigai is a Japanese concept that means roughly ‘something that makes you wake up in the morning’. Thomas Oppong’s short piece on Medium outlines how one can apply this concept for their life and their career. https://medium.com/thrive-global/ikigai-the-japanese-secret-to-a-long-and-happy-life-might-just-help-you-live-a-more-fulfilling-9871d01992b7
4. Algorithms to Live By: The Computer Science of Human Decisions is a great book to help you think more objectively about decisions (including career ones) that we humans make all the time, but which, frankly, computers tend to be better equipped to make. https://is.gd/Ap5keR
5. Be ready to go in length to get what you want. There are amazing cases of people getting jobs they wanted by figuring out the product & business and helping solve some real problems: Francine Lee got a design job at Dropbox by guerilla UX-testing & redesigning their Photos section, Nina Mufleh got a bunch of on-sites after her research with Nina4Airbnb website, and Philippe Dubost landing a PM job after having a huge success with his Amazon-styled CV website. Read more about it here: https://medium.com/the-mission/the-best-career-advice-for-young-people-96387eeb343a
6. Designers, if you don’t already read Julie Zhuo of Facebook, start doing it now. Julie has one of the best design leadership blogs out there, and she shares some good thoughts on career among many other things. Here is one of highlights: https://medium.com/the-year-of-the-looking-glass/how-to-think-about-your-career-abf5300eba08
7. Think about exec education. Hackernoon’s piece on becoming a product manager is great for that. Chances are, if yo work with very scalable matters (like technology) in any capacity, you’ll have to interact with product managers. You might even be in a role of one — knowingly or unknowingly. Here is a great article that can save you a lot of time (and money) navigating your work with or development of transferrable skills. https://hackernoon.com/forget-the-mba-heres-the-fastest-way-to-become-a-product-manager-b3a230a7c055
8. Be strategic about next steps in your career. Plan, invest time, build networks and relationships, execute on your vision. HBR’s piece on strategic career choices highlights what to do (and not to do) as you get to your desired outcomes. https://hbr.org/2016/12/think-strategically-about-your-career-development
9. Making decisions: learn to prioritize. Erica Meade applied design thinking to choosing a job opportunity. She came up with a great prioritization spreadsheet that I use to navigate my decision making process. https://medium.com/@ericalmeade/evaluating-design-opportunities-f2f9cc06b9c3
10. Cherry on a pie: inc. magazine’s collection of 25 inspiring and infamous leaders’ pieces of advice to anyone thinking of a career move. https://www.inc.com/business-insider/25-successful-leaders-give-their-best-career-advice-for-millenials.html