Failing to Succeed: Why I’m Shutting Down My Startup

And How to Set Yourself Up to Learn from Failure

Lex Evan®
9 min readNov 10, 2021

Failure is not something I have feared in the past. I have failed many times in pursuit of my ambitions, but this time it hit deep, and I struggled to accept it.
Admitting defeat is never easy, but the time is right when it feels liberating and not shameful. I have always viewed failure as a learning experience, and I hope this story will help you feel that way too.

Education and Curiosity: A Foundation for Success

As a child, I wanted to try everything — I have always been curious to understand how things work in the world. My mother encouraged me to explore my curiosity, but she never forced me to stick with anything when my interests shifted towards something different. Instead, she taught me to embrace my curiosity without fear.

What I have learned from my upbringing is that if you do not like something, you should not waste the little time you have doing it for the sake of doing it. If you try something and it does not bring you the joy you thought it would, it is okay to move on. The alternative teaches you to fear exploring your curiosity for the dread of continuing to do something you do not enjoy.

My mother also taught me that I could succeed in anything I set out to accomplish if I focused on my education. While she never forced me to stick with my waning interests, she was adamant that I complete my educational assignments. She never micromanaged me; she trusted me when I told her I had finished my work. Inadvertently, she taught me what it means to be an adult — to be accountable for yourself because no one will check in on you to do the things you need to do to achieve your goals in life.

Under a business lens, she was the best manager I have ever had — yes, I know it is absurd to think of my mom as a manager, but if you really think about it, isn’t that what parents do in preparing you to lead your own life?

My mother’s philosophy empowered me to nurture my imagination and explore my curiosity. Ultimately, I believe that is what makes me a great designer. And the self-accountability she instilled in me is what makes me a great leader. She gave me the greatest gift a parent could offer, a strong foundation for success that is not contingent on NOT failing.

Awareness and Intention: Failing to Improve

You will not be great at everything you do the first time you do it, so you must be aware that you will fail when approaching new skills. You must also not let failure catch you by surprise; otherwise, you will not be prepared to learn. Setting your intention to learn from failure will ensure you improve when you do fail.

I began my career in graphic design in 2008, one year before I earned my B.F.A. in Graphic Design with honors and my program’s Excellence in Graphic Design for Print Award. In the thirteen years since, I have led the design, strategy, and creative direction of global brands, products, and teams for some of the world’s most impactful beauty, health and wellness brands.

Failure has been the greatest fuel for my career growth and personal development through the last decade.

Doing the same type of work will only make you more efficient in how you do that work; it will not necessarily improve the work you produce. To improve, you must continue to learn new skills and be willing to fail.

Setting yourself up with stability and confidence is critical in embracing the mentality to improve through failure. You must be strategic in understanding the areas in which you may fail so that consistent failure does not leave you feeling debilitated.

I have maintained a passion for design and branding, but my curiosity has pulled me in other directions. Outside of work, I pursued my many interests through side projects and startup ideas with the awareness that I would not have all the answers or know-how to succeed right away. And with the intention to learn from potential failure.

I conditioned myself to view my success as contingent upon failure, not hindered by it. This perspective allowed me to overcome the fear of failing.

While my startup attempts did not make me the next Bezos, they produced insights that shaped me into a much stronger designer and a more efficient founder for my next startup attempt.

Strengths and Weaknesses: Learning Through Failure

I have read that investors are not keen on founders who have not failed because failure teaches you what you do not know and highlights the areas in which they can best assist you, your weaknesses.

Many people think the interview question about weaknesses is a trick question, but it is thoughtful and insightful.

If you are seeking growth, you must be aware of the areas in which you need to grow, and if you are hiring someone for the long run, you want to know how you might help them grow. Your strengths are what you bring to the role, and your weaknesses are what the person or organization you are partnering with can help you improve — understanding this when starting up is crucial to a successful endeavor.

I have launched five startups, to be exact. And I have failed each time, but I have learned through each failure, and I have come to understand my strengths and weaknesses intimately. For example, I know what I can execute efficiently and effectively, I know what I did not know I could do, and I know what slows me down and where to seek help. These insights have allowed me to shape and structure each new startup with more resilience for success.

When I was twenty, I launched an online magazine. That first startup taught me how to ask for help, manage people trying to help me, organize events, photoshoots, book talent, and get people to tell me their stories.

After that, I spent two years working on a design marketplace and design-project management startup to help connect businesses with design firms and creative freelancers. Through that experience, I learned to present complex ideas with simplicity, developed my public speaking skills, and studied the logic behind coding to build my own web app and communicate more effectively with developers.

The following year I took up fragrance development and candle-making, learning how to source raw materials, price products, find a market fit, and craft a resonating brand narrative.

Next, I began studying pastry every weekend for two years and full weeks during holidays, learning to be consistent and manage my time through concurrent tasks. I taught myself how to make all my favorite desserts through that journey, from macarons, profiteroles, and eclairs, to layer cakes, tarts, cookies, and pies, ultimately developing new recipes. Through this journey, I learned what drives people to shop and how to create demand.

This brings us to Alt Pronouns. The startup I have been running for nearly three years alongside my full-time job. I will post a detailed case study on Alt Pronouns in the future, but for now, here is the abridged version.

Passion and Purpose: Fuel for Success

My passion for LGBTQ+ activism and advocacy was awoken by the words of Lady Bunny when I watched The Out List in 2015. That moment set me on a path to uncover the history of my Queer identity. I learned how LGBTQ+ acceptance evolved through the decades and about the people who sacrificed their lives to make the world a better place for my generation. I thought I was brave when I had shared my Queer identity as a teenager, but in my quest for history, I discovered my courage flowed through me from generations of courageous LGBTQ+ activists. That is when I began thinking of how I would show up for future LGBTQ+ generations.

The initial idea for Alt Pronouns was born in the summer of 2018, and by March 2019, I launched on Shopify with 32 graphic t-shirt designs inspired by the Queer history I had uncovered. I created Alt Pronouns to bridge generations of LGBTQ+ activists and aid today’s liberation movements to create a safer, more accepting, and inclusive future for every human identity. I sold nearly $10,000 during the 2019 Pride season, and it felt exhilarating to see my passion and mission so well received by the world.

Shortly after launching Alt Pronouns, I broke my spine. I was still working my full-time job, and the sleepless long nights and weekends I had planned to spend nurturing my business turned into sleepless long nights and weekends of the most excruciating physical pain I have ever felt. It would take me eight months to accept that surgery was my only option after countless physical therapy and non-surgical treatments. After I recovered from surgery, an opportunity at work relocated me to Los Angeles to establish a new satellite design office.

I arrived in L.A. on Feb 1, 2020. Five weeks later, the world began to shut down. Covid brought the world to a halt, and I found myself alone in a new city, unable to socialize or connect with people; I fell into a deep depression.

Alt Pronouns was the last thing on which I could focus. Still, people found the site without any updates or new products, and I sold another $5,000 during the 2020 Pride season. I felt the passion for my mission resonate with so many LGBTQ+ people that it sparked an attempt to relaunch the brand in 2021. I rolled out a brand design update, new products and launched a community platform and publication called Queerist (which now lives here on Medium).

Despite my best intentions, my life and perspective were significantly impacted by breaking my spine, moving to a new city, and Covid and the protests that occurred that year. As a result, my life and the world had become much more stressful than in 2019, and I was no longer in a position to take on the physical and emotional toll of managing a startup with a strong, socially charged initiative.

The passion and purpose that once raged inside me, fueling my drive and dedication to give myself entirely to this mission, had come to a quiet flicker. Without that fire, I knew I could not sustain the required effort necessary to run a startup.

I needed to refocus on finding the peace and joy I lost along this journey.

Acceptance and Liberation: Knowing When to Fail

Alt Pronouns was supposed to be the last one — the startup that took off and allowed me to quit my day job and work for myself. It was going to be the “I told you so” to everyone who rolled their eyes at me starting yet another business. It wasn’t.

For months, I stressed over what to do. I struggled to accept that the time had come to shut down Alt Pronouns because I could not see my path beyond it. I have always had a new idea that pulled me out of the previous one, but I had to decide to give up for tougher reasons this time. I had to accept that I was no longer best suited to run this startup.

I have poured so much of myself into the brand that it felt like I would be giving up on myself. Worse, it felt like I would be letting down so many people who collaborated with me, donating their time and talents to bring this brand to life. I have felt the weight of their hope and optimism in me since day one, and it hurts deeply to let them know the time they invested in me and Alt Pronouns will not payout.

I built a large and ambitious ship and have run out of the fuel and passion necessary to move it forward. While my passion for the mission remains, the crippling stress, anxiety, and expectation I face daily weighed me down and hindered me from improving other aspects of my life. The mere idea of admitting defeat felt so weightless and free.

When accepting failure feels like liberation, not shame, it is time to fail.

Reflection and Analysis: Learning Takes Time

I know I have grown immensely from running this business — it has been my most successful startup to date. However, I also know that it will take time to understand what exactly this journey has taught me.

Reflecting on why I lost the passion for running this business was the first step to learning from this failure. In writing this story, I have found my peace to admit defeat without shame. I am excited to know I have become better prepared for my next idea; however sweet that may be. 😉



Lex Evan®

Founder, CEO & Chef @LexingtonBakes. 🏳️‍🌈 NB. Designer, Strategist, Writer.