9 Truths and a Lie
Unifying experiences of entrepreneurialism and the pursuit of professional freedom
Twenty years in and here’s what I know, I know nothing at all about Easy Street.
Once upon a time in 2004, there was a scrappy malcontent asking herself “is this all there is?” after only three scant years O-FFICIALLY using her college degree in the 9-to-5 world.
And when a possible canoe trip in the Everglades conflicted with the production of an association’s membership newsletter—which could have toooottttaaaallllyyy been auto-scheduled but my PTO was denied anyway, cue the drama-dots ... I saw my exit.
Goodbye, stuck-up office culture and fear-based leadership. Suck it policies and procedures that feel like a prison sentence. Sniff ya later, staff retreats, the conference room, and petty politics. From now on, I’m “working from the canoe.”
I was free!
You know what’s not free, tho? Rent. And so, it came to pass that <checks note> 2.5 nan-seconds later after coming back from said canoe trip, I hung out my shingle.
Rebecca Gunter, creative person. For hire.
Like, any day now. Yoohoo? Clients? I’m here for the if-you-build-it-they-will-come entrepreneurial package?
Oh, that’s not really a thing?
Well, whatcha got?
The be-so-valuable-that-you-practically-pay-for-yourself deal?
Question, tho….do I have enough ‘Wizard Points’ to get the grit and gumption required to figure it all out, essentially building the plane while flying, without ruining my reputation or starving to death?
I see.
So, basically, just go out on these kajillion side quests, many of which dead end in disappointment, and learn the universal lesson that the cost of self-made success is failure and the cost of failure is relentless experimentation and an unwavering commitment to your own ever-upleveling gold standard?
Seems straightforward enough….what’s that? Beware the River of Self-Doubt, you say? And the Village of Nonbelievers and Na’er-do-wells? I mean, when they say “it takes a village” that is not the village they’re talking about, is it Universe? I need a strong network I can count on who can also count on me.
Ok cool, cool…cool, cool, cool.
Oh, and brace myself for forces beyond my control ready to bring forth the chaos on a global, societal, and economic level, always changing, all the time? Every day’s a new reality, amirite, Universe? <chuckles nervously>
Alright.
The financial and emotional support of my friends and family and a solid lack of crisis, life changes, or competing personal priorities… I need that, too? Well, what if you don’t have that….per se? Go find it and/or learn how to get it all in healthy alignment, anyway, in spite of obstacles, oppression, and depression. Got it.
Is that it? Then, and only then, will I have what it takes to make it, like, for real?
Yes, Chef! I won’t forget to track it all. Because you can’t move what you can’t measure <dry cough>... that old chestnut. And of course, make sure I know my ICA better than I know the back of my own hand, get that messaging right, and always.be.closing, but don’t forget to give back to the community, generously and without expectation. Check! Check! Check! How’s my visibility? And my bookkeeping practices? Am I 100% sure I am the right business structure? Have I thought about hiring help or automating? Have I heard about ChatGPT? Well, it’s funny you should ask, Universe, because <trails off…>
I’d love to end this essay with “and that’s how she figured it all out” 🎬and roll the credits, but the truth is that I coulda played out that scene yesterday. Shit, I’m playing that scene out right now.
Because the more you learn about being a founder, a small business owner, and an entrepreneur—or anyone who has an ‘eat what you kill, uniquely responsible for their own quality of life and that of those of their families’ kinda thing going—the more you find out that you don’t, actually, know squat. Srsly.
If I’m honest, it’s pretty frickin’ nerve-wracking. And also, I wouldn’t have it any other way.
I didn’t get into this game for known quantities, guaranteed outcomes, or tried-n-true, the way we’ve always done it type a’ work-life. I want to break things, do it better, and give my clients and colleagues mutually beneficial advantages, ad nauseam. I want to make manifest win-win situations and rise the kinda tides that lift all boats.
In order to do that, I must get smashed against the rocks as many times as it takes until I figure out how to do more than just float and learn how to sail.
Or should I say sale? Because let’s BFFR, without sales there are no sails. There is only pure, unmitigated panic and one bad decision after another, up to, and including, your dreaded Plan B. (Which, for me, is bartending. Hard pass…lord willing and the crick don’t rise.)
I say all of that to say this: Twenty years in and here’s what I know, I know nothing at all about Easy Street, but I can tell you what I have learned trying to find it.
9 Truths about the Unifying Experiences of Entrepreneurialism and the (Com)Passionate Pursuit of Professional and Personal Freedom
Owning your own voice isn’t enough; you must also have the courage to use it.
My heart goes out to people who are afraid to really own their own voice. I’ve been there. As a creative copywriter, I’ve made a career out of being the world’s most delightful Gen-X, high-masking Autistic Cyrano de Bergerac this side of the internet. And yet, the less I let my own voice out of the box, the less rewarding work comes my way.
Despite being quite comfortable on the sidelines, thankyouverymuch, knowing who you are and why anyone should care can’t just be between you and your God—you must be brave enough to say it out loud, often, and without apology.Creative > Reactive. Period.
One of the most powerful things I have learned in my journey to DIY myself into sweet, sweet sovereignty and a bossless existence is that human development is within our control. Jennifer Thornton taught me that in a Human Development model, 60% of the entire population lives in Reactive Mode, triggered, scared, and unstable in the face of growth and conflict, whilst 30% of people live in Creative Mode, curious, collaborative, and endlessly effective in the face of chaos and change.
If you’re gonna do it anyway (i.e., be alive and try to exist in this kookie, messed-up world), you might as well be creative about it.Stepping into success isn’t destiny, it’s a decision. (Or, absolutely nothing that looks or feels like success will happen without Self-Belief.)
Be careful what you wish for; you just might get it. If you’ve been 🤞hoping for a business that you can survive on, you’re sure to get it. The problem is, you’re just surviving. Let’s try that again. Tell me who you are and why you’re the best in the world (it’s just that not enough people know about it…yet). Starting today, act like it.
Decide what kind of success looks and feels like by defining it for your own damn self. And now, you’re gonna have to choose to believe it. This is me now? Hell yeah. Now do what someone like that does, relentlessly, until you don’t even have to think about it anymore, you can just be about it.Even Riot Grrrls need routine.
I’ve learned that I am the most creative between the hours of 5am and 2pm, and anytime after that I suffer a sharp decline in hilarious and accessible chutzpah. Furthermore, if I’m not too careful, I can overwork myself into dissociating on the couch, completely drained of proverbial ‘spoons,’ glassy-eyed and binge-watching TikTok, waiting out bedtime when I can reset.
I’ve also found out the hard way that riding the razor’s edge of deadlines and deliverables is a lot less fun than it looks. No matter how many times I thumb my nose at regularity and routine, planning and doing things ‘on purpose,’ it holds true that the sooner we accept that only those with structure can scale, the better it is for everybody.Find your naysayers and put ‘em in their place…and it’s not where you think it is.
It’s my opinion that surrounding yourself with “yes” (wo)men is just about the most toxic thing you can ever do to yourself. If you’re a charismatic leader with great people power, it’s tempting to form an inner circle lousy with non-stop affirmations and positive feedback loops. Sadly, that house of mirrors eventually prevents you from truly authentic and considered decision-making.
Make sure that your inner circle isn’t afraid to dole out the just right amount of tough love, applied liberally when needed, and willing to offer the pushback that either makes a business case and defends your decision or gives you the perspective you’re craving to keep you grounded in your goals.Stand up and stand out in a Collaboration Nation. Team up with the tenacious, the underestimated, and the hyperfocused; that’ll be fun.
Your special sauce is a real gift. Once you’ve proven it to yourself and the world that your zones of genius and core competencies are worth paying for, it’s time to fly the nest and find your flock.
Because even the most extraordinary and masterful amongst us who have made a business out of our time, tenacity, and talent, we will reach the limits of our own capacity sooner than later. And when that happens, you’ll find yourself swimming amongst all of the other extraordinary and masterful amongst us out there doing the same dang thing we are. Adopt a more-the-merrier mindset, becoming known for playing well with others and you’ll outpace anything you could do solo. Look for other scrappy go-getters hellbent on co-creation and leverage the power of the collective.Form an avoidant attachment to Plan B.
Wise, peaceful and patient people tell us to always be running towards something good, not running from something bad. Fuck that, y’all. I’m all for the carrot on the stick, but I’ve learned that I’m far more motivated keeping a h-e-a-l-t-h-y distance between me and the velvet coffin of my “if not this, then that” escape route if <gestures vaguely> ‘all this’ simply does not bear enough fruit to live on.
Nothing motivates a dyed-in-the-wall entrepreneur to get their ass in gear like the threat of a 9-to-5, soul-sucking gig work, or taking ten steps backwards in the name of making money. Use that avoidant attachment to fuel your ability to make a living. Personally, I do not want to be forced to be great at making Cosmopolitans again, and that is very, very motivating.Be insatiably curious and committed to ever-expanding your mindmap with empathy and understanding.
Curiosity is my unique advantage. I believe that if someone has done it before, then it can be done. It’s simply a matter of finding out how and why. I also believe that in order to truly communicate, in writing, in relationships, in action, you must harness the power of perspective. By asking questions, following your intuition, you can develop the kind of acute mental acquisitiveness that makes it possible for insight and inspiration to blossom.
The more fluid and flexible you are in your willingness to learn, challenging your own limiting beliefs and seeing things from another POV, the more indispensable you’ll be wherever thought leaders, paradigm smashers, connectors and creative types are called for.
Always be poised to pivot.
Don’t like change? This life probably isn’t for you. To be an entrepreneur is to always mitigate vision with second-guessing yourself, the market, and the opportunities before you on a daily basis. It means striving for constant, non-stop evolution because that is actually the only way to thrive.
Whether it’s your first day with a brand new logo, freshly open for business or you’ve been grinding the whetstone of a seasoned, self-made career for two decades and counting, the sands are never stable beneath your feet. You’re not gonna wake up one day real soon and say, “phew! I did it. I figured it all out and from this day forward everything is totally in control and I have zero worries because nothing is ever going to change again.” Nice try, french fry; that is not a thing. The only constant here is change. On your marks…get set….GROW!
Life is too short for juicing fruit that isn’t worth the squeeze.
For me, entrepreneurialism is a genuine way to connect deeply with my own humanity and ability to live life on my own terms and by my own definition of success. The business arena offers me authentic agency and the kind of work/life sovereignty my freedom-seeking ass is tracking.
Whenever I hear this old adage, I have to laugh: Entrepreneurs are the only people who will work 80 hours for themselves to avoid working 40 hours for someone else. You got that right, Universe. I don’t wanna to be masked, mundane, or mediocre; ain’t nobody got time for that.
PS
Once upon another time I made the leap from hospitality to brand strategy, and that wasn’t pretty, ‘neither. Read about how skinned knees begat pivot-happy entrepreneurial energy, in “I Failed So You Don’t Have To.”
Watch why Jennifer Thorton, who taught me the life lesson in Truth #2, thinks that this should be our year to break things.
From waitress to wanderlust for the entrepreneurial arena, read my Origin Story from roots to Stoned Fruits. DJ, drop those dope drupes!
Pics or it Didn’t Happen
