Reflections from Main Street America

An Open Letter to Entrepreneurial Spirits

Life is increasingly tough and the timing will never be right. No matter how rough the seas, you are the captain. Steer consciously, live intentionally. 

Downtown Boulder Creek, California

Two years ago, I opened the doors to my brick and mortar gift shop, while working another job + last November I dove head first into solopreneurship full time. This small business journey has been stormy, and the past two years have knocked me over time and again. But every time I find my way back to the surface, I’m stronger and more able. If you’re considering diving into a small business endeavor, I hope that some of my learnings can help as a friendly light on the path. 

Here are five key lessons I’ve learned over the past two years: 

Check your ego at the starting line

It’s essential to obtain emotional maturity, breadth of skill set and financial stability FIRST before going solopreneur full time. Some folks are naturally gifted and their careers take off exponentially, seemingly with ease, but they are the exception not the rule. It’s best to be prepared because the path ahead will test your strength. 

In 2014 my twin sister and I attempted to launch a transportation service between San Francisco and Yosemite. We failed quickly for many reasons. At the honest core, I wasn’t ready. I wasn’t self-aware enough yet. I didn’t know what my values were and had an unrefined emotional intelligence (EQ). I had no savings or means of cash flow. Since then I’ve worked at over ten companies, for over twenty-five different “bosses” and gained a critical, sought-after skill set and finely tuned EQ. Growing up with entrepreneurial parents, I always knew that I wanted to be an entrepreneur, but I didn’t have a strong vision yet and clearly lacked business acumen. Good things take time. 

After opening my brick and mortar in November 2020, I continued working for my employer for the first year, as an executive assistant at a SaaS org, with their agreement. I’d log on, in meetings often and on-demand Monday through Thursday and then open shop Friday through Sunday. I had a handful of days off for an entire year.  I worked past the point of burnout but slowly and surely stored away for winter and invested in my small business. Gratefully to my husband, who provides further financial security and support in so many unrecognized ways, and for a few lucky past-employer stock occurrences, I was able to save enough to dive into business full time with a ~two year runway. Even coming from a background of middle american privilege, it took me over ten thousand miles traveling around America and ten years into my career to get to a place where I could dive off that deep end confidently. 

Author in front of storefront on opening day

Without a stable home environment, an amazing partner, a generous income that allows you to nestegg (or an angel investor if you’re lucky - I hear those exist but they seem like leprechauns in my experience), and a not-so-small amount of luck, overcoming the hurdles of building a small business can quickly become insurmountable. My small business journey started with displacement, as we were evacuated due to the CZU Lightning Complex fire, and my core demographic, Big Basin visitors, was curtailed for two years. Five business friends in my small community alone have recently been forced to close their doors. With climate change at the backdoor, it’s a tough world out there. Building in the pandemic also exacerbates every obstacle, and life events don’t stop, which will leave you with some really tough decisions. So before you pour your life savings, precious time and passion into a new endeavor, it’s best to make sure you’re ready. If you are lacking in any of these areas (EQ, skill set + financial security), start with self growth! 

 

How you live is who you become

When choosing your growth path, remember that how you live is who you become. Vision yourself in ten years, hopefully well into your business journey, and make decisions that lead to that version of your future. If you want to try out goal planning, check out this guide I wrote in 2019. There are a few pieces that constitute how you live: place, process and people. 

Where you settle matters. Migration is natural. National boundaries as we know them in the twenty first century, these borders that super securely separate us vs them, are less than one century old. Luckily state borders are liquid to United States residents - for now, let’s not take that for granted. I understand that moving to your desired location is a privilege; many folks are anchored by kids, careers, disability, being a caregiver, proximity to family, hardship... it’s still okay to dream and to build your own inner sanctuary a little every day. Unfortunately those with this privilege often squander the potential, as many folks stay in an ill-suited place and instead complain, complain, complain. If you’re unhappy with where you live, it’s time to start dreaming. You can get creative like Christopher McCandless or start with a mountain of research to help narrow down options. 

I grew up in the extreme weather and repressed nature of the Midwest so I longed for the West Coast and am a closet hippie so headed for sunny California. Ten years ago, after college and once on my own financially, I lived paycheck to paycheck as an adventure travel guide and had the time of my life. I lived in a 13-passenger van and trailer and toured up to 23 days and 8 National Parks in one trip. Exploring the vastness of land in these “united” states was a moving experience. Though ultimately with a couple years of vagabond life behind me, a deep desire for a home + the natural beauty of the SF Bay Area drew me in and love helped me settle here for good. As another quick real life example, my oldest brother raised his now-adult daughter in IL and then spent a few years traveling nationwide for seasonal work (including ranching, holiday warehouse work and beet farming), before resettling to rural Alabama with his wife, and they’re happy as can be. 

If you have the ability and freedom, you can work your way across America and find a place that feels like home. Again good things take time. There’s no red easy button for finding your serenity space. But if you take the time and plan right, you can build towards a locale more suited to you. And just in case it needs saying, climate change needs to be a key factor in where you head. If that’s a surprise to you, check out my Climate Conscious reading list on Medium

If you want to become a solopreneur, then along your path you’ll need to fill the gaps in your skill set without expectation or judgment: take a job in the service industry, work for someone you idolize, become a host at a state park, never stop learning - webinars, non-profit volunteering, peers, meetups, newsletters, industry-specific book lists, lessons come from all sorts of mediums. If you hate your job, try a new field. If you want to be a professional artist, I highly recommend Gianna Andrews’ new book. Keep experimenting until you find joy in work, know yourself + have understanding in the basics of business: sales, accounting, marketing, communications, logistics, and strategy (and/or the ability to delegate any of these). 

As you grow, two components will be key: time to process + mentors! Time to process is gold. In our over-saturated information-addicted world, it seems strange to just sit still and think but it’s critical. Our brains need time to process the stimulation constantly being thrown at us. Have you ever noticed how the best ideas seem to happen when we’re “turned off”, like in the shower or during a workout. That’s our processing power happening in the background. If you give yourself the space to think, it’s amazing how much more creative and less reactive we can be. For example, next time you walk, commute or do the yardwork, don’t listen to music or a podcast, just give yourself the space to think, to process. Not like in meditation where you aim to clear your mind, rather just let it flow. Whatever weird streams happen, let them come and see where they take you. 

Finally a good mentor is priceless. When you meet a game changer, you can learn life-changing lessons through years or in just one encounter. It can be hard to find a good mentor so cherish whatever little time you’re able to get and aim to provide some sort of value in return. Working for your mentor is a great example; I supported many of my best mentors as their executive assistant. If someone you highly respect grants you a meeting, even sending a simple thank you note or small thoughtful gift afterwards can be a meaningful gesture to show gratitude for their time and willingness to share their wisdom. Also another key way to honor someone's time (in all situations) is to be prepared: know what you want to ask them, take lead of the meeting and don’t waste a single second of their time. In addition to mentors, the people that surround you make all the difference. 

 

Community is everything 

Your inner circle defines you, and family is something that you get to define. It took me a long time to realize the latter. Everyone needs to unpack the messy scaffolding of our childhood + then offer gratitude for the deep roots that remain. In December of 2016, I took a moving workshop by filmmaker Barnet Bain, author of the Book of Doing and Being, who taught us how to unlock the raw power of our creative selves. It requires unpacking what you’ve been taught, since the very beginning - all the scaffolding used to create, repair and sometimes chip away at the edifice of the building that is you, and rewiring yourself to harness your energy and heed your true calling. What do you want to build; who do you want to be. If you want help digging deeper here, check out his book: The Book of Doing and Being. Once you’ve taken the space to explore this and tune into who you are as your creative self, you need to begin to nurture the next level: your inner circle. 

First off, it’s important to acknowledge that it’s okay to outgrow relationships; weed out any invasive roots or fear the whole foundation may crumble. I grew up in a large, messy, sometimes-dysfunctional family that rolled deep, with eight siblings and over fifty people often attending family gatherings. Since moving two thousand miles away and struggling through some trying times, the definition of family I knew in youth has been challenged in many ways. Today, family is a much more tight knit entity to me, something I wasn’t granted but rather worked hard to achieve. 

Many folks have said to me: tell me the five people you spend the most time with and I’ll tell you what kind of person you are. You are your inner circle so you need to appreciate them. After all, what you appreciate, appreciates. I’m proud of the folks that I call family and would do anything for them. Since opening my storefront and on top of some intense world happenings, our family experienced the birth of my niece, the loss of our beloved thirteen year old yorkie, and my husband’s battle with cancer. When you’re putting your soul into work, you need to check in with your core crew constantly and rebalance when necessary, without guilt or shame. When I was goal planning for this year, it was clear that my priority category in 2021 was Work so in 2022, I decided to put Play and Health first. Little did I know how critical that would become. Moving into 2023, I’m getting back into Work but putting Love before all. 

Having the flexibility to put family first has been my saving grace over the past year, and I’ll forever be grateful to my small business journey and our blessed circumstances to allow for that. This year really made me closely examine life, and I urge you to appreciate your blessings, whatever or whomever they may be. If your current work or lifestyle doesn’t allow enough space for your family, it might be time to reprioritize. If you’re lacking family, it might be time to go back to guideline two and start searching for your people. 

Beyond your inner circle, a greater community will have an immense impact on your life and business. As I mentioned before, where you settle matters and a massive piece of that is the community that surrounds an area. I’m so grateful to the Santa Cruz Mountains community for embracing my small business as they have. Find a community that sees you and appreciates what you offer, and then invest back into that community as much as you possibly can. Once you’ve found your people, lean into local resources: newspapers, radio, chambers of commerce, volunteer organizations and social clubs. I was honored to recently be featured in our local newspaper, the SLV Post, especially since my marketing to date has mostly been organic. I haven't had Facebook for over ten years, never have had a TikTok and I haven't spent any money on advertising in the past six months so local PR is a big deal. Life is all about genuine connection. I truly believe that the future is local so the more you can focus energy locally, the more sustainably your whole ecosystem can grow. 


Be ready to do the work 

Being your own everything in a small business is a lot, to put it mildly. Don't wish for it; work for it. If you expect a payoff anywhere less than three years in, you might find yourself in a really tight spot. It’s all about building slowly one building block at a time with great balance. Your foundation needs to be level. This journey will be a marathon, not a sprint; pace yourself so you don’t burn out before your time. In building a small business, you’re constantly juggling the needs of design, marketing, customer service, sales, packaging, strategy, finance and everything in between. 

As I mentioned earlier, I worked myself past breaking point, and it’s taken its toll. It took nearly half this year to get my mojo back (through lots of play!), and then my husband entered the weird world of cancer, which is a whole other beast (and a topic for another time). If I hadn’t found my footing and committed to balance, these past six months would have knocked me out. I may be bruised and battered, but at least I’m still here swinging. 

volunteer trail building on Santa Cruz coastline

If you can afford it, set aside some time for volunteering. It’s a win-win; in addition to making an immediate impact on your community or a non-profit project, it can be very re-grounding + you can learn an abundance of peripheral knowledge. If you’re looking for a volunteer opportunity in Santa Cruz County, I compiled a list of some of my favorites. I was able to volunteer over 100 hours in 2022, and those days out on the land were some of my highlights of this year. Volunteering is a great way to invest in your community, especially if you have time but are resource constrained. 


Culture is a feeling

This one is best summed up by the amazing Socrates Rosenfeld. Brand and culture are about creating space to feel. "Culture beats strategy ten out of ten times.” In late 2019, as my current role was in turmoil, I sent an open application to Jane Technologies and received a note back from the CEO, inviting me for a meeting. A note straight from the CEO from a simple open application; I was astounded! I had worked in tech, in SF and Silicon Valley, for over four years at that point, but walking into their office in Santa Cruz was like a breath of fresh air. The feeling was subtle but welcoming - in a world that idolizes technology, it felt refreshingly human. The meeting wasn’t a job interview really; it felt more like a counseling session almost. That meeting was what really inspired me to pursue my mission for this shop. That’s the power of a mentor, in even just one meeting. And impressively without any follow-up (besides a thank you note of course!), Soc was one of my earliest customers. 

In building my shop, I’m not trying to build an empire or a million dollar business. I’m creating a feeling; aiming to inspire folks to harness their energy consciously. If you’ve ever visited my shop, I think you might know what I mean. It’s about being honest and present. It’s sharing my spirit and passion with everyone who stops by. It’s about celebrating our open spaces and this amazing community we call home. 

Learn how to stoke the flame; energy is power. If you can learn how to harness your energy or how to inspire others to focus their energy, that’s power. Aim to wear out, not rust out. Remember you must die; but right now, you’re alive. You have energy. Feel your breath, your heartbeat. Use your being for good. 


Gratefully

Thank you for reading my reflections! I look forward to many more learnings ahead. If you’re on an entrepreneurial path, I’d love to hear your insights ♥️


This journey may be dark sometimes. Wherever you are tonight, I’m sending you a little light + wishing you the best of everything.