Navigating uncertainty: a life off rails

Exploring Lake Powell, UT—August 2019. Most of the hiking we did here was off trails.

On this episode of Kristen’s Headlong Dive Into Entrepreneurship, I’d like to talk about transitions. Starting Meaning, Inc is one of the biggest transitions of my life. I’m finding it difficult to clearly articulate what the experience is like—in part because it’s still happening. But let’s give it a try!

Something I’ve returned to is the concept of living a life on rails—following a preconceived approach for how I am “supposed” to move through life. Until recently, my journey went something like this: study hard in school, find a clearly marked career path to follow—one promising a strong likelihood of success, and then work hard and stick to that path. That said, there was always an undercurrent of “do what makes you happy”.

I supplied my own criteria for happiness: help people and grow personally. Of course, I didn’t do this alone. I had the help of my family and friends, teachers, and life experiences. Reflecting back, I’ve always felt strongly about helping others and personal growth—I’m lucky and grateful for having support along the way to follow my gut.

Before Meaning, I pushed myself to the edges of my comfort zone but always within the constraints of the rails. Only taking on risk I thought I could successfully manage; narrowly defining the space within which I could explore. I thought I needed these boundaries in order to operate, to avoid feeling overwhelmed.

😳Expanding my view of life and work

A lot of things lined up to expand my work/life view. I saw the rails were constraining and it was possible to live in a more open way, trusting my happiness criteria:

  • I met Dave who had been living his life off rails for almost twenty years. I was encouraged by the work he did and the people he met along the way—his style felt alive and free, guided by his instinct not anyone else's agenda.
  • I began working remotely and found a professional flexibility I didn’t know I was looking for. I knew I was able to manage my own workflow, but doing remote work under the leadership of Brian Burwell and Paul Saucier gave me the chance to stretch my skills and grow into my professional confidence.
  • Dave and I decided to move to California, my first time living outside of the midwest. This was a big “leaving the nest” moment for me, and helped break out of my play-it-safe mindset.
  • I started meditating to manage my stress and anxiety. Meditation found me in the run up to our California move, and I have since habituated a daily practice. This has been an evolving experience, and a lot of fun. I share a few of my favorite meditation resources below.
  • I started a regular yoga practice, one that has grown into a daily morning routine to wake up and ground myself in my body. I swear by the app Glo: they have so many amazing teachers, and different styles of yoga and meditation.

My journey is just beginning and I’m excited to share insights as they emerge from the chaos. For now, let’s fast forward to present day and take a look at living a life off rails.

🎢Learning to embrace feelings of uncertainty

So far, my biggest lesson in starting a business is to embrace uncertainty. To avoid the trap of believing I should have any idea what I’m doing. A much more productive mindset is that of trust—trusting my skills (problem solving, research, analysis), my business partners, and the process of discovery.

This approach results in half of my time being fun and games—it’s fun to trail blaze! Leaving the other half akin to rock climbing without ropes. A seemingly impossible task coupled with feelings of exhilaration, flow state, and fear of death. I exaggerate only slightly.

Alex Honnold climbs El Capitan free-solo style (no rope). Photo credit to Jimmy Chin. Yosemite National Park, CA—June 2017.

There’s something about making a decision without being certain it’s the “right” decision that triggers a panic response. I attribute this panic to my changing attitude toward decision making—moving past the concept of right vs wrong and into a mindset of make-the-best-decision-based-on-information-on-hand. My favorite way of describing this new mindset is courtesy of my 92 year-old grandma, Baba, “do the best”.

Taking a peek at my “do the best” approach

Over the past few weeks, there’s been quite a bit of activity in the Meaning world of accounting, legal, and finance. I’m building out the pipelines for how our company operates, and I’ve never done this before. Embracing uncertainty and doing the best I can, I’ve made decisions to keep Meaning moving forward. To get a flavor for what I’ve been up to, here’s a look at some of our recent happenings:

👾Contract work for a front-end developer. Until now, it’s been Dave, Gustavo and I, and our lovely Meaning community. We needed some front-end dev support, so we contracted a developer to help us out. Luckily, our friend’s multimedia production agency works with a developer who they vouched for—it’s nice to know we’re hiring good talent and working with people we trust (Heyyyy Thinko 😘).

Still, there was a contract to read and sign, so I put my legal hat on. For this task, we didn’t need to have our lawyer review the contract. I could easily take care of the job, but that doesn’t mean I ENJOY contract review. Legalese is the worst, a byzantine maze of language. And it’s stressful - am I supposed to actually understand what this is saying? I understand enough to sign the dotted line.

📑Another contract! Introducing the SAFE—the Simple Agreement for Future Equity. The SAFE is an off-the-shelf convertible equity contract, which is a fancy term for an investor agreement. Not going into all of the nuance here, though it’s a nice little investment tool. Getting familiar with the terms in the agreement was a challenge, things like discount, equity, liquidity, capital vs. preferred stock, etc.

I worked with our finance advisor, April, and with our lawyer on this one, confirming the template met our company’s needs. Ultimately, the SAFE was ready to use with very minor edits. Dave, Gustavo and I represent the entire Meaning Board of Directors, and we agreed to using the SAFE to govern the terms of investment.

💰Juggling investment logistics. Dave’s investing a small amount of money into Meaning to get the Hopper prototype built, pay for our monthly recurring expenses, and cover necessary costs for the founding team. This seed investment is designed to get us going and solidify our business plan.

When talking money, I usually put on both the finance and accounting hats. In this situation, we had to transfer money from point A (Dave) to point B (Meaning bank account). Easy enough. But wait! Are there tax ramifications for taking this kind of investment? Quick, consult with our accountant to confirm that no, this kind of investment is considered a loan or a debt, and won’t count as taxable income for Meaning. If it was, I’d push out the investment to 2020, so we wouldn’t have to pay taxes until 2021. All of these small considerations add up and require quite the juggling act.

Lastly, on the money front: updating our financial runway. Organizing the company’s monthly expenses, one-time expenses, and balancing those against our seed investment. Some of this is estimation, some of it more known. I’ve been playing with the numbers to see how far we can stretch our initial investment. This is an ongoing exercise that will adjust with the reality of cashflow in and and out.

Adding structure to guide the uncertainty

I thoroughly enjoy organizing this mess of legal, accounting, and finance. It’s satisfying when things start coming together—building systems and structures to operate our business. There’s a distinct cycle of moving from the unknown and uncertainty, to something that feels more ordered. It sure takes a lot of time and mental effort to pull this off, to make sense of all of the moving pieces. I continuously remind myself that I’m doing the best I can.

🧘🏻‍♀️Meditation Resources

Before I conclude this week’s newsletter, here’s a few meditation resources that have helped me along the way with life’s transitions:

  • I first learned mindfulness meditation techniques in Logan Square in Chicago through a 6-part class at a holistic health clinic.  The teacher recommended a free app which includes guided meditations, music meditations and a timer: Insight Timer.
  • The meditation guide Rupert Spira was introduced to me through Dave when he was exploring the landscape of meditation techniques. Rupert hosts meetings and retreats, guiding folks through meditations. The first meditation with Rupert I sat through had a major impact on my experience of day-to-day life. I found having an understanding of mindfulness was helpful before diving into Rupert’s meditations.
  • In habituating a daily meditation practice, I’ve found the 10% Happier app to be super helpful. I like the different courses offered, on topics like basics of meditation, emotions, and healthy habits. There are a number of different, well-known teachers to select from, too—which is great, every teacher has a different style. In particular, I enjoy the meditations to help with relaxation and sleep.
Sibling pic! Lincoln Memorial Reflecting Pool, Washington D.C.—December 2019. ❤️

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