How to choose your next role

Every designer knows the beauty of constraint. Choosing what to work on is just as important as choosing what not to work on. 4 years ago, when I was considering leaving Google to start a new company, Hunter Walk shared this forcing question “What are you optimizing for?” Money? Power? Influence? Free Time? Personal Growth? I’ve come back to his question every time I’ve had to make a decision about career and life.

“What are you optimizing for?”
— Hunter Walk

The people and relationships in your life will always be more important than the day-to-day work you do.

“What are you optimizing for?” I want to have my cake, eat it, design it, and magically multiply my cake for tons of other folks to enjoy too.

Break Your Life Down

When faced with a fairly tough choice about what to do next in your life take, take a moment and think about what you would like to optimize for in your life.

Here are some key categories to consider:

You — What do you need to be physically, mentally, emotionally and spiritually happy each day? Make sure each day you’re drinking enough water, spending the time you need for psychical activity and mental rest.

Family and Relationships — What roles do you currently play in the lives of others? Friend? Sibling? Father? Mother? Partner? Son? Daughter? How can you structure your life to have the time and energy to dedicate to your roles in a way that brings you happiness?

Money — Money can sometimes be a huge part of taking a new job for most people. Ask yourself: what are your long term financial goals? Write the numbers down and figure out how to get there. Are you willing to take less cash and more equity and make a bet on a new company? Would you prefer more cash at a large established company? Consider the long term earning potential of your role — be sure to consider bonuses, stock and promotion tracks along with other benefits like travel, healthcare and the klout that comes with a certain role.

A few general thoughts on money— Having money doesn't equal happiness, but not having money brings stress and hardship. Debt is crushing. Don’t spend more than you make. Cutting expenses is much easier than increasing your revenues. Have the courage to get your spending under control and you will find peace of mind.

Work and Career Progression — What would you like to do more of? less of? Do you want to continue in your craft as an individual contributor? Lead a team? Switch careers? Start your own thing? Careers and work have huge impacts on every aspect of our life. For example, when I chose to raise money and start Design Inc. I was so focused on the business that my relationships with family suffered. After I closed Design Inc. I had a great deal of family debt to pay back. I needed to put everything on hold for 6 months so I could reconnect and repair the strain I had put my family through.

Ryan Lessard offered this model for thinking about new opportunities

There are no right answers here, what works for you may not work for the next person. More importantly, don’t compare your journey with someone else. Your happiness and importance has nothing to do with how you stack up against others. Be honest with yourself, pursue what you truly want in life and ignore the haters.

Thanks for reading! I’d love to hear your thoughts on how you’ve made the big decisions in your life and how you think about optimizing your own life.