My Best (Mis)takes: A year of full time entrepreneurship
If you know me at all, you know I am unapologetically optimistic.
It is borderline annoying.
I grew up enduring medical challenges, one after another, including eleven reconstructive surgeries to repair a cleft lip and palate (a genetic birth defect) chronic migraines and late stage Lyme Disease. Surgeons cut me, then I spent weeks, months, years, healing, repairing only to be cut again.
I am grateful for this cycle of extremes because it gave me my optimism, grit and self-awareness. Traits that make me intensely reflective and cause people to describe me as an ‘old soul’.
Over a year ago, I jumped into full-time entrepreneurship as Sitterly’s Founder and CEO. As the anniversary came and went, I turned my reflective eye on my mistakes and successes, only to realize they are two sides of the same coin. This article is my take or performance review of being a full time entrepreneur.
As my own boss, with only the market to review my performance last year, I absorbed harsh feedback, exciting wins and a priceless education. As I listed mistakes and successes side by side they began to align and plot a course, like a treasure map charting an adventure, they told me a story of where to go next.
As I listed mistakes and successes side by side they began to align and plot a course, like a treasure map charting an adventure, they told me a story of where to go next.
My best (mis)takes after a year of full time entrepreneurship…
10. Scaling too fast. The truth is, I thought I got lucky. The imposter in me said, ‘You got lucky. This won’t work somewhere else.’ I set out to prove the voice in my head wrong more than five times over. I’d pick a new market, develop the brand, print flyers, set up the site then walk university campuses getting students and families to sign up. Consequently, I ended up with 5 small businesses and 14 requests to expand with little infrastructure to support them. Proving the concept 5+ times over helped develop a better understanding of target customers and product. However, I did not deploy enough patience to build systems to sustain the business. Moving forward, instead of sufficing in many markets, I’ll be focusing on one until it operates independently. I am putting my process engineer hat on and exercising delegation muscles past managers say I lack.
9. Assuming my friends and family have the same risk tolerance. Truth is, my leap into full time entrepreneurship scares the shit out of them. Conversations with family and friends are those of noncommittal support with a vague undertone of doubt. Their words come from a place of love, wanting me to be safe. Entrepreneurial colleagues warned me about this strain. Experience made me understand it. My greatest doubters and supporters are the same people, starting with myself. When people tell me I cannot do something…I tend to do it. I made a habit to over communicate my purpose and goals, but stop short of trying to convince. My grit and optimism enable me to turn frustration into gratitude; gratitude to have people who love me and want me to be safe.
The greatest pleasure in life is doing what others say you cannot do.
8. Not engaging with my community enough. I did engage mentors, mentees, staff, customers and colleagues, but nowhere near enough to truly connect or understand problems and create efficient solutions. In retrospect, the best ideas, stories, and insights came from non-scalable interactions. I gain more energy from interacting with people and bringing them together than I do staring at a line of code on my computer. Recognizing this, I am pivoting to focus on the experience, filling my schedule with one-on-one interactions, adding new real time chat features, and regular events.
7. Not paying enough attention to the experience, on and offline. I assumed community members, customers, mentors, mentees, customers and colleagues would forgive occastional hiccups. Truth is, some are more forgiving than others and errors damage brand. In a weird way, servers crashing and bugs in the code provided an opportunity to engage with customers and members in an impactful way. For example, an email complaint (admit it we all get them once in a while) provided an opportunity to deliver above-and-beyond customer service, solving the problem quickly and with overwhelming generosity. I received touching testimonials after these exchanges and extracted patterns that inform my way forward. Realizing one-on-one interactions generated more impact, meant taking a closer look at the user experience from end to end, online and offline. I believe the ‘experience’ economy is at an inflection point, about to skyrocket, and I, and the communities I build, will be on top of the wave.
6. Not making myself accountable to anyone. People say, ‘That so cool you can do whatever you want!’ My response, ‘Exactly. No one to blame but me.’ Complete freedom is as paralyzing as captivity. Unstructured days gave me freedom to explore, to work from anywhere. However, venturing into the unknown also required tried-and-true routines to lose consistency. I find great inspiration while exploring new geographies through long hikes, runs, bike, train, and plane rides. All the while listening, watching and observing. My appetite to learn proves insatiable as a constant flow of books, audiobooks, podcasts, and writing enabled me to explore my own mind, skills, weaknesses and tendencies. It is in periods of unstructured freedom I come to know myself, connect with new people and find a new level of creativity. I call them collisions. They enable me to leapfrog ahead, instead of spinning my wheels in monotony. But, I also recognize the value of routines and consistency. I established more measurable routines and Key Result Areas for myself, the community and staff. I found mentors and took on more responsibility as an advisor and mentor to students. Writing this article is an example of how documenting the journey helps to better communicate my goals and hold myself accountable at scale.
5. Waiting to hire & delegate technical development. Somewhere along the way someone said ‘You are a woman in tech!’. I did built my websites, for better or for worse, without formal training or technical background. My high pain tolerance and resourcefulness is a blessing and a curse. I beat my head against technology longer than most, learning from the misteps eventually succeeding. On one hand, I saved money, gained technical skills to create websites and was able to cheaply beta test different models and features. On the other hand, I created inefficiencies, slowing innovative development. I avoided wasting investor dollars on overpriced website designs, but gained valuable domain knowledge. Now, I have a firmer grasp on the model and my own strengths. I am excited to be in the final stages of hiring this out to someone with more technical skill.
4. Not holding staff accountable to my own standards. My father tells me I am too hard on myself. Mentors tell me I am ‘too nice’. While I hold myself to impossibly high standards, I struggle to impose the same on others. I operate in extremes and find it hard to ask others to do the same. Although, I know they will thank me for it one day. I find it difficult to impose extreme standards because I know it is painful to achieve them and true grit is in short supply. Unfortunately, this resulted in average performance from staff and compromises on my end. In reponse, I changed the hiring process, I no longer ask for resumes, but for strategies, videos and examples of work completed. I developed an intense onboarding process and learned to hire slow and fire fast.
3. Thinking my runway was long enough. One angel investor told me, ‘whatever you think you need…double it’. He was right. Ambition is expensive! However, the education I earned in one year of full time entrepreneurship is priceless, worth more than my college degrees, more than any certificate or corporate tenure. Moreover, I unintentionally became more minimalist, realizing money and possessions do not motivate me. I turned down multiple job offers, gave away everything, moved in with family, lived on savings and poured everything into the business. I learned to pull at the opposing levers of practicality and ambition.
I learned to pull at the opposing levers of practicality and ambition.
2. Compromising on my health. It turns out, living out of a suitcase and hopping my way around the country isn’t great for sleep or fitness. However, it did bring a lot of opportunities, experiences and connections. Health is a like bank account, and I made withdrawals to invest in new opportunities which are already producing returns. I know what ‘great’ feels like and I have big deposits to make to get back to feeling great. In part, I developed a mindfulness practice that helps me manage the highs and lows of entrepreneurship. The body is built to endure and mine is tougher than most. Being an optimist, I am excited to see myself transform again as I train to complete my first Triathlon.
1.Getting caught up in my own ego. Overwhelmed with opportunity, my excitement fractured my focus. The (albeit small) attention, headlines, labels and compliments made work fun. More importantly, I now understand the discrepancy between who I want to be and who others want me to be.
I now understand the discrepancy between who I want to be and who others want me to be.
I wrote this article to step into who I want to be: I am a humble and ambitious bootstrapping entrepreneur with 2 life goals:
- Live to see two centuries, without regret(1 down 1 to go)
- Fill a football stadium at my funeral
Some expect me to fold, and slip into a safe narrative and pretend these mistakes never happened. Others expect me to front and explain away my mistakes with petty blame and excuses.
Remember, I am an old soul, tough beyond my years.
I love the journey more than the destination.
Truth is, I am just getting started.