Almost Reckless: A Creative and Pragmatic Approach to Taking Risks - Hardcover

Smilovic, Amy

Hardcover

ISBN 10: 0593854799 ISBN 13: 9780593854792

Publisher: Portfolio, 2026

Synopsis

“Almost Reckless is not just a book, it's a permission slip. It's about the courage it takes to step off the algorithm's path, the clarity that comes from defining your own principles, and the joy of building something that feels unmistakably yours.” —Will Guidara, bestselling author of Unreasonable Hospitality

Amy Smilovic's cult fashion brand, Tibi, was a thriving $70 million business when she realized she was working toward someone else's idea of success. So she threw out the rulebook of how things should be done and went with her gut instead.

Today Tibi is more successful than ever, and all on Smilovic's groundbreaking entrepreneurial terms. 

In Almost Reckless, she invites you to get comfortable with embracing smart risks in pursuit of your own vision. Sharing her story and drawing on her years of helping others identify their values and principles, Smilovic teaches you to hone your gut, and your trust in it.

With humor and practicality she coaches you in how to determine what success means to you, including:

• why you don’t have to listen to the data guys
• why you should be a Creative Pragmatist
• why sticking to your principles isn’t incompatible with success
• why work/life balance is bullshit

Almost Reckless is the essential blueprint for entrepreneurs, leaders, creatives, and anyone who wants a working life that feels aligned with who they truly are.

About this title

About the Author

Amy Smilovic is the founder and creative director of Tibi. She launched the brand with $15,000 and no formal fashion training in 1997 and today helms a company that is vastly different than the one she, or anyone in her industry, could have envisioned. She is the author of The Creative Pragmatist, a wife and a mother of two sons, and describes herself as feeling content. Very content.

Excerpt. © Reprinted by permission. All rights reserved.

Chapter 1
Running Toward Something

Recently, I put out a question to my followers on social media: What risks would you take if you knew it would all work out?

The responses were varied. People would quit jobs, start new businesses, ask for promotions, even move to faraway countries.

I then asked a follow-up question: What does "all work out" mean to you?

The answers had resounding consensus: They all assigned a numerical value. Interesting.

Around the same time, I'd done a few interviews on my (Almost) Reckless podcast with highly successful entrepreneurs who'd taken dramatically different paths. Every single one of them said frequently that they framed their decisions, their appetite for risk, against their "breakeven." That number didn't assure them that the future decisions were right and would guarantee they would flourish, but they understood where the line was drawn-the worst that could go wrong-and not to cross it.

For them, knowing it would all work out meant knowing first how to define what it means to not work out. But this break-even number, while important for a business, only tells you what failure is. It doesn't help you understand what you're running toward. And if we don't know that, it's hard for us to know when we've arrived.

In order to do big things, understand truly how much you're willing to risk, you must first figure out for yourself: What does it mean to all work out? There's a problem with setting a number as your goal, though. Numbers are a moving target, a form of measurement that, just like international currency, can be quickly devalued. Today's quest for $3 million may be tomorrow's inflation-adjusted quest for $5 million.

Ultimately, you need to drill down to the very core of who you are to know what happiness and contentment look like for you. To define how you want to be. You need to know your principles, using them as the measuring stick for making bold decisions or simply giving your gut permission to lead the way.

It's your gut check, defined not as a rumbling feeling but in real words.

Your principles give you permission to gauge success for yourself, to see industry standards as immaterial. They give you freedom to think about possibility. They're what help you logically and, ultimately, help you intuitively understand the next steps that are right. For you.

Eventually, for Tibi, we identified three principles that, if adhered to without fail, would ensure that we were on the path to contentment. The financial breakeven was done, of course. That's our line in the sand. (More about that later.) But the principles are what keep the guardrails in place for moving in the right direction. They are the assurance that moving off path and taking steps that are wildly different from those of our industry peers is part of a bigger plan.

I can't tell you what your principles are (and if you think I can, then you're misunderstanding the premise of this book). But I can tell you mine, and how they got that way.

Different and Better

"Pack up the gerbils and the kids, we're moving south."

I'm not sure that this is exactly how that conversation went, but that's what my parents did. At the time, my sister and I were six and eight, and we lived outside Chicago. My dad was working in my uncle's psychiatry practice in Oak Brook and took weekend and evening shifts at emergency services in a mental health center in a city hospital, and Mom was a teacher at one of the local schools. We had a small two-bedroom apartment; my sister and I had bunk beds, and we'd tie a rope around the top bunk to reenact scenes from Batman. I was Bruce Wayne, and my little sister had to be Robin the sidekick; as the elder, I gave her no choice.

Life was just fine. If Mom was really tired, we got to eat Taco Bell after ballet class, and I had found out that by lifting up the sod around the common areas of our apartment, you could find lots of earthworms. I could sell the worms to other kids for fishing, for unregulated scientific experiments, or just as pets.

Why in the world would my parents want to leave this slice of heaven?

My grandmother was sobbing, hearing the news. How could we do this? We were close enough to my grandparents' home in Indiana for a Sunday lunch or two. My cousins were one town over. "Why would you leave us? Don't you love your sister?" Grandma asked my dad. "Yeah, why don't you love me?" my dad's sister asked.

My dad explained. He and my mom weren't running from something; they were running toward something.

My parents shared a common sentiment: They felt their happiest, their most content, in the time spent with each other and their kids. Time was measured in the activities my parents loved doing, like the weekends fishing at Bill's lake. My grandparents' little fishing shack there had a working kitchen and one bed, everything we needed for a full day catching bluegills, my sister and I napping while my dad and grandfather fried the fish in Grandpa's famous beer batter. Or like the afternoons when my dad taught my sister and me how to sketch, so we'd spend time with him but not have to occupy his full attention-he'd make sure we had our own pads and pencils.

And even still, trying to earn an income that would help my parents pay for our small two-bedroom apartment required my dad working at Chicago's psychiatric ward on the weekends to earn additional income. They were living the definition of a bifurcated life, the days obligingly muddled through to get to the weekend.

It wasn't just that the weeks were divided between work and then life, or time with family. It was also that they were viewing their future life in this way: the hard struggle years where they would toil, endure, and miss out, and then the comfort years when we will have made it. Now versus then. Today versus tomorrow. This morning versus this evening. All of them disconnected, clearing your head to be present and then check out when leaving so you can focus. Snowed under for months of the year, a long commute to the city, and no unwavering belief that what they were working toward would make them truly happy drove my parents away from the region where they'd both been raised.

So no, my parents weren't loading up a peace-sign-stickered VW van and checking out. We were just moving to St. Simons Island, Georgia. A place where my dad could practice his profession, Mom could teach, and they could arrive shortly after we got home from school, where my sister and I had let ourselves into our apartment with our own keys hanging from strings around our necks that bounced around as we skipped home from school, a short half mile away. A regular weekday would include a round of tennis, maybe a morning coffee watching the sunrise over the marsh, and it definitely involved a family dinner at the table where I complained I was sick of eating the shrimp we'd caught the past weekend seining down by the pier.

And each summer, we'd head back up to Indiana, our moss-green wood-paneled station wagon, just like the one found in any Chevy Chase Vacation movie, bursting with camping gear because we didn't have cash for hotel rooms and besides, isn't that more fun? (My parents' words, not mine.) Our dogs were loaded in; a kennel for a month was out of the question. And little Igloo coolers were jammed with bologna sandwiches, saltines, premixed Kool-Aid, and a carton of milk to mix with our cereal at a picnic table at the rest stop somewhere near the Kentucky border-thirteen hours of sustenance in one cooler.

Would I have done the same myself? Yes, but no. The exact specifics of location, vocation, mode of transport? I don't think so.

But rejecting a bifurcated life, running toward something I knew was right even if no one else could see the rightness? Yes.

The same ends, in a different and better way.

Reckless-almost.

The Cool Parents

In retrospect, the vibe my parents gave off was at odds with the reality of how they parented. My parents were sarcastic, funny, and, when I reflect back (because no one can really see it at the time), cool. They were young. They were smart. They were fun: Every Halloween, they'd dress as different characters from an SNL skit-the Coneheads, Dan Aykroyd and John Belushi's Bees, Bill Murray and Gilda Radner's Nerds. My dad looked the part of a bit of hippie. If you looked at my dad in the mesh tee he'd bought to mimic what John Travolta was wearing in Saturday Night Fever (a disco had opened up on the island to tap into this raging trend), you'd be forgiven for thinking he looked a bit irresponsible and devil-may-care, when in reality he was deeply principled and anything but.

But for all their coolness, Mom and Dad were so solid in communicating and living their core principles that my sister and I knew, instinctively and through experience, that if they said something, they meant it. When our loaded-up car was halfway to Disney World and my mom whipped around from the front seat to yell at my sister and me, "If you punch each other one more time, we're turning the car around"? Well, we punched the shit out of each other three minutes later, and so at an exit in St. Augustine, Florida, our Ford station wagon turned around and headed back north. If they said it, they meant it.

But it wasn't until later in life, and after having kids, and especially after running a business, that I realized how well my parents struck that balance, and how much of an impression it left on me. They could be the cool parents-I mean, they had me at twenty-one-but they weren't permissive. They had those unwavering core principles that underlined every decision they made. Case in point: In seventh grade, after we'd lived in Georgia awhile, I got a job delivering newspapers on my ten-speed bike, ten dollars a week. I discovered a hideaway along my newspaper route that was the perfect place to stash a plastic bag filled with four packs of cigarettes-three I'd bought from the vending machine at the hotel near the beach and one I'd swiped from the chimney of my grandmother when she visited from Terre Haute, Indiana. It was a discovery significant enough to make it to my diary: I detailed my profound thoughts on the different flavors offered by Virginia Slims and Newport Lights. I even convinced (she would say bullied) my neighbor to visit my secret stash, where I taught her to smoke; neither of us inhaled. (But you've heard that before.)

Shortly after one relaxing smoking session with my neighbor, her dad came to visit. My stomach churned; I felt I possessed a sixth sense that something bad was going to happen. Turns out it doesn't take a sage to figure out that the kid next door ratted me out to her parents when she came home smelling like a bar.

My parents called me into their bedroom; it was the only sort-of private place in our house, and it doubled as our room to be counseled in. My dad asked if I knew why I'd been called in; my face didn't require an answer.

He went on to ask me what it was that I loved about smoking. Was I exhausted after a long day of tossing papers and needed a break to soothe my nerves? Maybe it was the rush of nicotine that helped me reflect upon a weary day at school juggling kickball games and geography quizzes?

My dad's sarcasm wasn't my only punishment. That smoking escapade cost me two weeks-grounded with no phone and no TV. My pleas and counterarguments-that my grandparents smoked, that I'd even seen Mom smoke one time-went nowhere. I was being grounded for lying-not the kind of lying where they asked if I had smoked and I said no, but what they called "lying by omission." They said every time I came in the house after my route, I was lying. (You can see why I would have struggled to think of them as cool at the time.)

Still, some of my friends' parents, in all their Southern decorum, perceived our house to be the wild place-the badlands. We were the Yankees who had moved to the South from the morally bankrupt North, where no one was required to say "Yes, sir" or "Yes, ma'am." We were allowed to see an R-rated movie, as long as an SNL cast member was starring. And we weren't required to go to church every Sunday, though we often did and would then have to endure car rides home with Mom unpacking the conflicting views of Carl Sagan, the big bang theory, and creationism, imploring us to always poke and question.

Contrary to their parents' perception, however, my friends knew the truth about our house. They knew there were limits, where the lines were drawn, and what could get you expelled: drugs, racism, and Reagan. And interestingly enough, the Reagan ban was lifted when I started dating someone so grounded in his own principles, a nice guy who worked obsessively hard at his family-run pizza restaurant and would speak passionately but calmly to my parents about trickle-down economics. Here, perhaps, was someone to set their troublemaker elder daughter on the straight and narrow.

For instance, this boy-I'll call him "Reagan" here, for short-and I were hanging with my friend who was working at the local drugstore. When we walked out the door, she handed me a thirty-cent Blow Pop.

A mile into our drive home, Reagan asked if I'd paid for the sucker. I explained it was just thirty cents. He turned the car around, and said I had to go back in and pay. I told him it was ridiculous, humiliating, and where did he get off telling me what to do. He said I could do whatever I wanted, but that he owns a business, businesses are people, and it's as if I took it directly from someone's pocket. It is wrong to steal.

I explained that I knew the pharmacy made so much money, the pharmacist drove a Lincoln. Proof. Hah.

But no. This was a deal-breaker for him. It wasn't about the thirty cents; it was the principle of the thing. And he was deeply principled.

Then there was the night of the high school basketball game. Frederica against Savannah Country Day. At halftime, Reagan had presented his school's principal with a ten-thousand-dollar donation from Pizza Inn, their family restaurants. We went out to the refreshments area, and a table was set up handing out Domino's Pizza; they'd just opened on the island, fast delivery, everyone was talking about the hamburger topping they offered. My seventeen-year-old boyfriend turned around, went back into the game, and asked the school's principal for the donation check, which he calmly and confidently took and folded into his pocket, then walked away.

Edition details

• Publisher: Portfolio
• Publication date: 2026
• Language: English
• ISBN 10: 0593854799
• ISBN 13: 9780593854792
• Binding: Hardcover
• Number of pages: 272