The Cleveland Flea

One of my proudest achievements, this venture swiftly transformed into a sensation, launching me on an unexpected, eight-year adventure. Though unprepared, this journey has become a profound source of gratitude for me. It unfolded as an unfiltered examination of the entrepreneurial ecosystem, complete with its imperfections. This experience was instrumental in shaping a new approach to business—one focused on minimizing drama and fostering deeper connections at its core.

The most important insights I gained from this beautiful business experience: Meaningful Work Matters, Inner Creativity Shared Joyfully is a Powerful Force for Connection (Emotional & Financial), and It Takes Considerable Intention (and Energy) to Keep it Going Well.

1

We thrive on consistent connection to creative folks who are excited about their own creative work beyond just paying bills or solely amassing more wealth.

2

We often struggle in adequately supporting these creative folks even though their thriving benefits our own desire for consistent creative connection.

3

We thrive in our careers / work when it goes beyond being something that just pays the bills but isn’t solely focused on solely amassing more and more wealth.

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We struggle in creating that type of work for ourselves, the kind that we’re invested in creatively and emotionally, whether that’s in our own business or our career.

What continues to strike me in working with clients and supporting my own small business friends is just how disconnected so many still say they feel– despite having an abundance of advanced tools that provide accessible interaction, and a potential for more free time and extra money than we have ever had in the history of the world. We just aren’t that good at being together in a way that brings us closer. We don’t often seem to use the resources we have to bring us closer together, even though that’s what we claim we’re missing. These things feel fundamental, essential, necessary.

What I have also learned is that until we look inside our own minds and reckon with the emotions we have when practicing work and life together, much of what we aspire to will still remain frustratingly out of reach. Yes, it’s absolutely possible to mine from within a valuable offering to bring to market that will not only offer you greater purpose in work but that will support your basic necessities (and more) and facilitate connection to another human who can find similar value in that offering. This should be a great option in a market economy.

So why is it so much harder than we want it to be for so many of us?

Don’t have time to read all the articles? Here’s what rose to the top of this 8 year unofficial study.

More– Insights, Highlights & Lowlights

*An important note: When I say ‘We’ it should be noted that what I mean by that is anyone operating within the framework of unchallenged, unseen, blindly-adopted White Patriarchal Capitalism. Most of us adopt this system as the default, but it is by far not the only way to work toward business success. Also, I include myself in this assessment.

We as women bring way too much shame (worry, anxiety, low self worth) with us into business.

We don’t know how to effectively have conflict in our lives and businesses.

We often have too little understanding of our own privilege and abundance.

We bring too much fear with us into business.

Many of us are living in functional freeze or fight or flight–
and running businesses from there.

Very few of us bring a higher power into our businesses, and instead work to create a cult of personality rather than working within our God or Universe-given talents and interests .

Very few of us come to business with (or learn) the essential skills required to bring safety our inner worlds so that we may live our values and work toward goals in a nourishing and non-oppressive way.

We put people on pedestals and judge people harshly in ways that are unkind and unhelpful.

Lessons Learned & Insights Gained– About Us, About Business & About Our Relationships

After all of this work and research, my belief is that Connection is better than Disconnection, and that Better Connection Intentionally is a starting point that sets us in the direction of success in many areas of life and business. Is it easy, zero-problems path? No. But is it worth it? Absolutely. This work begins with Self.

What We Lose When We Overlook Self-Care in the Pursuit of Business Growth

Cultivating Genuine Connection: Unpacking the Essence of True Community– And Should We Even Want It?

The Effects Instagram Has Had On Us 12 years later And My Own Predictions Of What Is Going To Work

The State Of Relationships: The Shopper & The Business Owner

Most People Just Want Jobs, And That is Just Fine!

The (Totally Unsurprising) Ways Our Personal Lives Shape Our Business Success and Struggles

What You Think About Other Business Owners Has A Pretty Profound Effect On Your Own Business And Life

Do We Want Collective Growth and Empowerment Or Do We Just Want Drama? It’s Hard To Tell.

Shift With Success– From Shopper Mindset to Business Owner Mindset

The Threshold That Is Great To Reach For Is The One That Allows Your Business To Care For YOU, Too.

How Cultural Narratives of Failure and Scarcity Influence Entrepreneurial Journeys In The Worst Ways

The Unhealthy Norms in Startup Culture That Make Business Harder

Transformative Moments: How Great Reckonings Reshape Us and Our Businesses

If We Want A Strong Ecosystem, This Could Be A Good Way To Think About It

The Story That Entrepreneurship is Easy is Really Unhelpful, and so is The Story That It’s Hard.

PERSONAL INSIGHTS

Going Viral & Gaining Overnight Success

One is intensely-feared, the other is intensely-desired, and they are both highly dysregulating.

Becoming an Overnight Sensation for the Wrong Reasons: My Experiences With Online Backlash and the Lessons Learned

That Time My Business Went Viral and Shoved Me Right Into Extreme Business Growth– For Better And For Worse

What has become abundantly clear to me is that keeping people happy and ensuring they judged me favorably became more necessary than caring for my own basic needs, let alone my dreams, desires, or future.

REFLECTIONS

Here are a few of the things I would have done differently, if I had a time machine of course.

Rewinding time isn’t an option, but if it were, I’d have a few do-overs up my sleeve. It’s with a hearty chuckle and a pat on the back that I look back—not in regret but in a ‘high-five, we made it’ kind of way. Here’s a toast to the past me, from a future friend. Who knows, maybe you’ll spot a gem in here that speaks to you, urging you to march to the beat of your own drum, even if it's slightly offbeat.

  1. I would have taken my ENTIRE year 2 off to actually build systems. Yes, this would have upset and shocked people but if I would have done this, I would probably still be in this business today.

  2. I would have made my first business hire a bookkeeper. And I would have gotten into therapy right away, without shame. I would have challenged the part of my brain that said I didn’t have time or money for these initial essentials. It simply wasn’t true. And I would have worked with my therapist to effectively partner with my bookkeeper.

  3. I would have stopped listening to other people more than I listened to myself. (recovering people-pleaser here!)

  4. I would have limited my growth to a pace my body could have handled, even though that would have meant disappointing others.

  5. I would have found and hired a business coach who aligned with my values.

  6. I would have done my best to run my business from my physical, emotional and financial capacity– not from a place of people-pleasing.

  7. I would have prioritized the creation of a Business Emergency Fund.

  8. I would have paid myself without shame. I ran another business to pay for my own salary and bills and essentially volunteered my time for free for my business because I felt ashamed and wrong for making money. It was a real shame.

  9. I ran my business equally as an ideological project, and though I’m grateful for the research it provided, I sort of wish I would have just run it as a more cut and dry business.

  10. I lived in so much drama (personal / financial / social / business) and I think that took away a lot joy, money, and success. I would have worked to find the help I needed, though I don’t actually know that I could have found those resources. I think we have far more support now in these ways than we did before.