Let’s start with a truth no one wants to print on mugs: starting your own small business is not a polished, sexy leap into financial freedom. It’s a chaotic belly flop into a sea of uncertainty and you’re lucky if you don’t find yourself deep under water.
While big start-ups boast glossy pitch decks and a boardroom full of caffeinated venture capitalists whispering sweet nothings of seed funding, the solo small business owner is usually paddling through open waters with nothing but a dream duct-taped to a lifejacket and the vague recollection of a Vinh Giang lecture I watched half-awake at midnight.
It’s not glamorous. It’s not easy. And most of the time, it’s not going to look like you know what you’re doing. But if you ask me? That’s where the magic lives.
Let me explain…
Huatulco, Mexico
Picture this: I’m in Huatulco, Mexico for a hot vacation. The air was a heavy heat – I think it was over 40 degrees that day. I sign out a windsurfer from the resort booth, buckle my lifejacket and proceed to rekindle my love of windsurfing on the Pacific Ocean. There are massive cliffs behind me, the open waters in front of me and an entire beach resort full of pasty vacationers starboard. I never pretended I was an expert. No swagger in my walk, just sheer determination.
What unfolded next can only be reserved for a quirky Adam Sandler movie: sunburned vacationers watching with a passive curiosity usually reserved for a weird wildlife siting or a slow-motion trainwreck.
I’m doing this thing because once, decades ago, a cute boy taught me how to windsurf on Sylvan Lake. Yes, Sylvan, where the water is so shallow it’s basically nature’s bathtub. But I learned. So naturally, why not pick up where I left off… 30 years later…in the ocean, with salt spray in my eyes and a margarita hangover.
This is a small business origin story – a situation I find myself reliving today.
I Was Out There Alone
In a small business, there is no team in sight, no financial committee, no Gantt chart, no TED Talk-worthy pitch. Just me and maybe a supportive loved one who sends me “you got this!” GIFs every few months. My husband mumbled to me as I left the cabana that morning…. “Don’t drown please.”
Starting small isn’t just about scale. It’s about solitude. It’s about waking up at 2 a.m. wondering whether you’re a genius or completely delusional, often scribbling down ideas under a tiny light in a notebook labelled “Do the Things”. It’s about being the admin, the CEO, the janitor, and the social media intern simultaneously.
In a small business, you’re windsurfing solo, and the board’s not going to sail itself. Okay it might, but it’s not fun if you’re watching it move further away from you, knowing you lost your deposit.
Some People Will Never Notice. That’s Fine.
Let’s be real: half the beachgoers never even looked up. They were too busy scrolling through overpriced mojito menus or reapplying SPF 70. The same goes for your business. Not everyone will care. Your cousin won’t repost your launch. Your neighbor won’t understand what you do. Your old boss will tell people you’ve “gone rogue.” Companies and former co-workers will never return your emails.
It doesn’t matter. You're not doing it for them.
Proceed as if You’re Prepared to Drown
Okay, dramatic—but not inaccurate.
Wiping hair and salt out of my eyes every time I fell and plunged into the water is something I think about often. I fell hard. Repeatedly. If you didn’t know any better, I would say I fell with such vigor and conviction, it looked like it was intentional.
In your small business you will inhale metaphorical ocean water. You’ll question your life choices while your website crashes during peak traffic. You’ll mess up invoices, miss deadlines, cry in the car, and wonder why scammers keep telling you that your website isn’t ranking number one. Which is funny because the scammers (up to 10 a day) are finding me quite easily.
But if you're prepared for it—not terrified, just prepared—you’ll stay in the game longer than anyone banking on smooth sailing.
Never Give Up: The Cliff Is Behind You
There’s no going back. You’ve told people. You’ve maybe even posted about it. You’ve invested money and time and your heart. Most importantly, only you will know if you really gave it your all.
Just like the cliffs behind me in Huatulco: impressive, immobile, and definitely not climbable in flip-flops, I’ve committed. Giving up now would mean drifting backward with the current into the rocks. So, forward it is.
Calm Waters Don’t Actually Help You Move
Any activity on a warm sunny day in smooth waters might sound appealing—but without wind, you and your windsurf aren’t going anywhere.
Same with business: comfort zones are creativity vacuums. You need friction. You need stakes. You need those cringey emails with spelling errors, awkward networking events, and terrifying public speaking moments to develop grit.
Try. Fail. Repeat. Then Repeat Again.
I fell off the wind surfer for a solid hour. The snot situation was real. Every plunge into the water was less majestic than the last. And yet… I kept climbing back on that board.
In small business, this is the holy grail of endurance. The ability to keep showing up when the applause hasn’t started, the revenue isn’t flowing, and your confidence feels like a deflated giant flamingo floaty in a warm kiddy pool. Keep doing the things.
Experience might get you up there. It’s belief that holds your balance.
I knew I could do it. I had history, after all, you know, that one full day windsurfing 30 years ago. My repeated failures were all real time experience. I didn’t blame the board, the wind, or the universe for conspiring against me. I believed in the possibility. That tiny spark—quiet but persistent—is what pulled me up and kept me upright. In small business, believing isn’t everything, but it’s the start of everything.
If There is Applause, it Often Comes After Success.
After waterboarding myself for over an hour, I finally made it up on the wind surfboard - sailing for a solid three minutes - parallel to the beach (potentially by accident). With the wind in my fish-soaked hair, the sound that came next was disarming and a true adrenaline rush. The roar that echoed from the beach was hundreds of people cheering and screaming. I looked around. I was the only idiot in the choppy waters that morning. The target of the cheering was not misinterpreted. The loud eruption was a mix of support and disbelief that I finally made it up on the board. Remember this sound followed the hour of silence while I was systematically drowning myself. Now, in this moment of victory, the support and shared success was undeniable.
The moment you finally have enough momentum to declare any success, that is likely when the cheering will start. Be prepared for this. It is not ingenuine, it is just how it works. It is the safest way for others to support a small business owner. The moment where strangers celebrate your sheer determination and refusal to sink.
Success might take longer than an hour of flailing in the water. But it will come inevitable if you don’t quit (and yes, wear a life jacket, just in case). True success is not validation from pasty beachgoers or Instagram likes. It’s knowing that despite all odds, you did the damn thing.
Reflecting on Our Experiences
Starting your own small business is rarely elegant and never easy. It demands endurance, humility, a touch of recklessness, and a whole lot of belief. It requires you to dive into unfamiliar waters with nothing but muscle memory and stubborn optimism keeping you afloat.
There will be cliffs. There will be doubters and doldrums. There will be days where calm feels like success… but isn’t. Every fall is proof you’re trying. Every attempt is progress. And every person who cheers from the beach is a reminder that even the lone windsurfer can make waves. Folks love a good story of determination. So, buckle your metaphorical lifejacket, grab the board, and sail straight into the chaos. There’s glory out there for anyone who dares to try.
True story.