What’s Inside The Box?

(This post was originally published on my blog at schlaf.me)

I recently had an exchange with James Beshara, Founder of Magic Mind and creator of Below The Line Podcast, about having a multi-path career.

Embarking on a multi-path career has been a big adjustment for me. Not even a year ago, I had a single career as an institutional investor. This was my life and identity for nearly a decade. The transition from VC to coach, angel and creator has been incredibly life-expanding but also challenging.

Each month, I spend countless hours collaborating with dozens of founders, executives, and creators. On a given day, I could be helping a founder navigate a tricky co-founder relationship, listening to a fundraising pitch, studying to become a more complete coach, and/or curating resources for the Founder Library. That’s just skimming the surface.

For the first time in my career, there are far more requests and opportunities flying at me than I can even process. Coaching inquires. Podcast invitations. Fundraising pitches. Advice requests. Networking intros. Since I’m a people pleaser and suffer from FOMO at times, I can become overwhelmed especially when I’m processing email and reviewing my calendar.

I’m now at a point where I have to say no far more than ever before. Otherwise, I won’t have the time and the space to focus on what truly matters and energizes me. I’ve come to appreciate that my inbox is essentially a task list for other people. Because I’m a solopreneur and I have a multi-path career, I need to be ruthless with my time or else I won’t get much accomplished.

Alongside my coach, Chris Sparks, I decided it was finally time to develop a series of filters to determine what I say yes to and how I invest my time. I call this my box. It can never have more than three main activities or projects inside of it.

My box currently contains:

• Coaching
• Angel Investing
• Founder Library

As Chris and I talked through these three core activities, we thought it would be useful to create an acronym to ensure it was memorable. We landed on CAL — coaching, angel investing, and library. I liked the simplicity of this. I also liked how CAL is an abbreviation of calendar. What I say yes to ultimately impacts how I spend my time, manage my energy, and make progress on my goals.

In true Chris fashion, he pushed me to double click into each area to determine what falls inside of my box. Here’s a summary of what I came up with.

I also defined what falls outside of my box. At the moment, these include things like random networking meetings, new project / product ideas, pitches that don’t fall in my strike zone, and catchups without a purpose.

If it’s a “hell yes” then I can move forward and allocate the time and energy towards it. If it’s a “yes but not right now” I can determine the appropriate timeline to engage. If it’s a “no” then I can quickly decide on the next action (pass or ignore).

Given my box is more now clearly defined, I’m able to quickly determine if an opportunity or request is one that I should prioritize, kindly decline, or punt on until a later date. This helps reduce the cognitive load while processing email and DMs. Most importantly, I’m able to be far more effective and efficient in allocating my time.

These filters have also been useful because I suffer from ADD and shiny object syndrome. New ideas, projects, and relationships energize me. Given how I’m wired, I’m unable to add anything new to the box without removing something. This forcing function has been incredibly powerful. If something doesn’t fit but energizes me, I now simply write it down so I can revisit down the road.

Through this process, I’ve come to recognize and appreciate that I have the power to decide what goes inside my box. Its contents can absolutely shift over time. They’re never fixed. New opportunities emerge. The context of my life evolves. Energy pulls me in a different direction. Life is fluid and dynamic.

Here are some questions that I’ve contemplated over the past year to help me gain more clarity and determine what fits inside of my box:

• What are the activities/projects on my plate right now?
• What activities/projects are critical, aspirational, and/or a waste?
• What do I want to optimize for personally and professionally?
• What activities/projects energize me and/or drain me?
• What are my highest value activities/projects?
• What activities/projects give me leverage?
• What activities/projects utilize my superpowers and zone of genius?
• What compels me to say “hell yes” or “hell no” to an opportunity?
• Who do I want to become in 3–5 years?
• What’s my five-year vision? How do these map to that?
• What three items fit in my box? What’s most important? Why?

I’ve found these questions to be incredibly insightful as I’ve navigated my own multi-career path. I often ask these questions to my coaching partners, especially those in a transition or struggling with how to focus. I hope they serve as a starting point to help you determine what might fit into your own box.

The older I get the more I realize that setting boundaries is one of the most important things you can do if you want to accomplish your goals and bring your vision to life. Going through this process with Chris not only helped me set tighter boundaries but also clarified my filters. I’m now able to get more done while also maintaining my sanity.

The multi-career path is incredibly intoxicating and fulfilling. I’ve never had so much fun professionally. I’ve also never been so productive. But this path requires ruthless prioritization, intense focus, and a strong commitment. It also requires saying no and disappointing others. For the first time in my life, I’m ok with that because I know what I’m focused on.

What’s inside your box?