Creating your future life

After a much needed career break, I started reflecting on shaping the next phase of my life. Rather than focusing solely on my job or career, I thought about who I wanted to be and the kind of life I wanted to live.

These are not easy questions, nor should they be, but you have to start somewhere. Often the hardest part with existential questions is just knowing where to begin. For me, I fall back on making lists. I share these not as a framework or system, but as a starting point for you to think about where you might begin.

What do I want to do?

The world is your oyster, so what do you actually want? This exercise is about tuning into yourself, dreaming big and small, allowing yourself to be ambitious, silly, comfortable. I wound up writing serious things, like working with a purpose and including creativity in my day to day. My list also included personal, playful things, such as having my kids color in my tattoos with markers and one day owning a house with a basketball hoop. I want to practice piano, sit courtside at an NBA game, and ski in Japan.

It's OK to want things and not know if or how they'll happen. In fact, figuring out that puzzle is the point of this whole exercise and is deeply fulfilling. Remember, this isn't about just work, it's about you.

What is holding me back?

Here's where you confront your demons, where you try your best to be honest about what's stopping you. While external forces play a role, these barriers are often of our own making, fears and obstacles that only exist in our mind. Seeing those and naming them can not only be therapeutic, it can help put them in perspective and not feel so big and scary.

Examples from my own list include being my own worst critic, but that criticism almost never helps and leads me not to start things. Sometimes I'm distracted (thanks ADHD), and sometimes I feel like I have to do a thing perfectly because I only have one chance.

This list is vulnerable and important.

What am I confident in? When am I comfy in my own skin?

When I first wrote this one, I titled it "What am I good at?" only to realize that's the wrong framing. I wanted to focus on when I felt most like myself. That has nothing to do with being good or not; it has to do with being able to do a thing and enjoy it for what it is, to enjoy being you.

Personally I feel most comfortable when I'm finding the essentials of what needs solving, when I'm building relationships, and when I'm getting rid of what doesn't work (for me or for the problem I'm solving). I trust my inner voice, I have a good ear for music, and I enjoy sharing with and serving others.

This list was the hardest one for me to write, as it requires viewing yourself with grace and valuing who you are. As difficult as that may come, being a friend to yourself is going to help you build the life you want.

When am I happiest at work?

OK fine, we have to talk about work at some point. We all have bills to pay. That said, instead of focusing on a specific industry or job title, think about moments that you've been the most fulfilled in your career. What kinds of work have been the most rewarding? What people or situations brought the most joy?

My list included being able to build things and make good decisions quickly, prototyping ideas, socializing with coworkers, helping others succeed, and learning from discussions with customers.

When am I most unhappy at work?

Of course, we need to think about the opposite, what we don't want. Instead of writing a list of complaints, I chose to reflect on times and situations where I was the least comfortable.

We've all had bad days at work; this exercise is more about what consistently makes you unhappy. Some examples from my list: endless meetings (especially video calls), busy work, feeling the need to appease leadership, and when the rest of my team is unhappy.

I'm not a big fan of focusing on what you don't want to do, but knowing what red flags to look for is important. The last thing you want is a job that takes more than it gives.

These lists helped me get my mindset in the right place, focused on my whole life. I also make sure not to edit the list as I write, to let my thoughts flow no matter how random. Tapping into that stream of consciousness is important, as you can find patterns you may not see if you try to overthink things.

I hope some of this resonates with you. What exercises do you find useful when approaching big life questions? These are very personal moments, so be open to finding what works for you. If you'd like to share yours, please get in touch as I'd love to hear.