People ask me what age demographic we design for and if we make things for younger or older customers. Know this, when I say “people” I mean either editors or other fashion industry professionals - especially marketing or branding consultants. You know who never asks? The people who wear my clothes. Or simply Creative Pragmatists. Here’s why. Because every morning when they’re getting dressed, each time they’re considering a new purchase, they’re critically thinking rather than thinking critically.

Here’s the difference. Critical thinking means they’re applying their experiences, their current situation, and their preferences to weigh out what is best for them, right now and for the future. Thinking critically means you’re fixated on a varicose vein or worse, someone elses. I say worse because no one wants to be a judgey little MF.

I’m a big fan of applying reason to the reason why we do things. In case you haven’t read it yet - Almost Reckless (here)- my new book helps you break this down, with how to/action steps, and apply it to all the areas that reside outside your closet. Your career, your family, your happiness and ambitions. And if you’re like me, they’re all deeply connected and one and the same.

So how do I view dressing your age? I don’t. Here’s what I mean - if you view age and clothing in isolation, then you could look at this and think here’s your directive for age 20, 40 and 60.

But the thing is, these are three different individuals entirely, in terms of their personal style. And since personal style is an amalgamation of everything here below, I can state that hot pants here on the left should never succumb to lounge lady on the right - and someone with those loungey inclinations would have felt deeply out of place at age 20 in the shiny shorts.

So image 1 here. Can you tell her age? If I zoom in on the college paraphanalia, I’m going to guess around 20.

Or this one here. She looks straight up to me like the new version of Working Girl. That late 20-something on my subway ride, WSJ hanging out of her bag, eager to get stuff done. This is my lens, anyways.

And now here- she could be anywhere from 30s to 40s (again, my lens)- we go from the bride on a honeymoon, the navigating a wardrobe while pregnant, and having the perfect item for sticky, clingy hands.

And here we find ourselves, the kids are a bit older and we’re standing by the sidelines at a soccer match. The plaid shirt and sandals have all the chill for a busy mom in her 40s. And on the right, they kids have now fled the coop - and the pants that did all that hard work is now the one that is worn when our other 50+ group comes over for my whipcream vodka signature martini.

And now I’m approaching 60, and I’m headed to exercise class - no longer in search of the hot body but rather one that has enough muscle to strengthen bones that have gone to shit.

And here I’m imagining my life in my 70s and 80s. My brain doesn’t have to expand too far, I pick up these ideas from the incredible women I get to meet everyday now - whether IRL or in my DMs. I’ll be on the boards of various companies and get to talk about some things I’ve learned, what I know - but I won’t have to write up anyone’s reviews and for that I’ll be so damn grateful. And hopefully if I’m lucky I’ll have some little grandkids putting their sticky hands on top of the stains I’ve lovingly kept from so many years ago.

So you see, age? It’s not a thing, not when it comes to clothes.

Here’s the beauty of critical thinking. You really begin to question the rationale for things. Why would I be limited to (xyz)? Why wouldn’t I wear what I feel great in? Why on earth would I let someone else’s limited view of age limit my own?

Now, getting back to Almost Reckless…..

you can see how thinking about ourselves and our style through this lens overlaps in to real life. Because as I mentioned earlier, these questions about age come about from those within my industry. Which has me thinking, exactly what industry am I in? I know the answer to this now, and it’s amazing when you figure it out. Almost Reckless helps you get to that point, promise.

In 1996 just before I left for Hong Kong, I told my parents I was going to quit American Express and that I’d be starting a designer brand. I had no design experience save working in a boutique in high school; but I loved fashion, I could draw, and I had an understanding of marketing and business. I showed my parents my initial sketches of the pieces I was going to make. To this day I can’t show them to anyone, they’re that embarrassing although they are a bold testament to what belief and determination can make happen. My parents said something like “you can do anything you put your mind to” and off I went.

And that was the easy part, because saying I could do something versus truly supporting me are two different things.

And for this, I am forever grateful to my mom.

When I called in 1998 for my mom to help me with my business, she answered. She worked full time as an Assistant Vice Principal at my old High School. Admittedly she had no idea what she was getting in to. But neither did I. And that is the point, she just jumped in there with me, even though everything about it was truly inconvenient, hard work, and required a deep belief that it would all work out. Maybe my mom is the O.G Almost Reckless?

Mom “officially” retired from Tibi a few years ago, but in a way truly never has. I don’t have her packing up boxes and following up on unpaid invoices, but she’s there on the other end of the phone supporting me everyday as my biggest cheerleader. And as time marches on, I hope I will be there for her in exactly the way she was for me. As someone who loves her dearly but I need her to know, that I’m there for more than just supportive words. That showing up physically is part of the bargain that I owe her in return. It is a debt I’m here to repay, happily.

I’m going to begin here with an excerpt from Almost Reckless. This will help frame the mindset behind this discussion:

I grew up in the 70s and 80s. We were like free-range chickens, allowed to wander, explore. Peck around at various opportunities. All ones that individually made no sense and were no indicator of my future. But totaled up, they told a far different story. No one asked me at age 12 what I wanted to be when I grew up, and they certainly didn’t craft my extra-curricular activities and align my tutors to ensure the right college so I could get the right advanced degree for the right job in the right corner. And somehow, at the same time, I wasn’t aimless. Somehow all of this added up to founding Tibi, what’s now America’s largest and longest standing independent designer fashion brand.

Jim, my brother-in-law, has his own law firm after spending 25 years as a prosecutor in the U.S. Attorney’s office. My sister called me recently, she was watching Jim in closing statements at trial. She said watching him pace in front of the jurors, every skill he’d honed teaching high-school history in between college and law school to earn money for tuition was brought to bear on a jury that had very complex information broken down for them as if they were 15 year old students. Couple that with Jim’s time spent coaching his son’s basketball leagues, the jury was fed this information with the enthusiasm of an NBA half-time locker room session. And yes, Jim went to Princeton undergrad, but so have thousands of other lawyers. Yet he’s one of the most successful lawyers in the country, while others are not.

A recent article in Harvard Business Review titled “Soft Skills Matter Now More Than Ever” articulates that companies prioritize this skill set when they’re hiring for long-term retention. Remember, companies, the great ones, are never stagnant. Truer now than ever. Because for someone to stay and thrive at a company, they have to be able to see the bigger picture, pivot, and grow.

If you look up the definition of “softskills” it’s presented as the non-technical, intangible personality traits that determine how someone interacts with others and behaves in a business situation.

I asked AI how I can acquire them:

Utter bullshit.

I wonder, is the specificity of this so enticing to people? The answer above wraps it up so neatly. Yet I’m 100% sure this is not where life happens. And softskills can only be acquired when you’re living your life, they can’t be preordained. They’re happening at you when you don’t even know it. But, in order to receive them, you have to be in the right state of mind. Present. Almost Reckless lays out a blueprint for how to get in the right frame of mind to collect, identify and codify your soft skills.

And think on this. If softskills are that important to a company, maybe you can understand how important they are for us in our lives? If you are the company of you, then being able to learn, grow, and pivot is an essential skill set. Especially with the acceleration of change. Clear-eyed and steady wins the race, simply because if you are those two things, you’ve already won.

If you love supporting independent booksellers (we do) then you can order the book BY CLICKING HERE:

Joking, but not really….

But, but, but…when people share your mindset, how they think about things rather than what they think about things, that’s where good discourse comes - the kind that inspires you, helps you problem solve, move forward. This is my definition of feeling settled.

I’m framing this to make my point. Stay with me here.

Recently I posted a video and a woman wrote in: “bad outfit. Just being honest”. We are in a time in the world where we can receive hundreds, thousands of opinions at warp speed. If you are an entrepreneur, running or working in a company, or just finding your way as to what is next for you, it’s impossible to separate the bad noise. We’ve let these people in to our lives. One individual, one who may not look anything like a friend you’d want, or a potential customer or client, has the ability to send a message that gives them equal status with all others.

You think.

But the reality of the algorithm is, these individuals have outsized status. It’s simply gamed that way. Good for the Metas of the world, bad for humans. Unless you break away from the algorithm and understand who is in your community of customers – who are your potential customers, you’ll continue to experience mental whiplash. That whiplash is destabilizing because it dulls our gut and you lose your instinct for what is good or bad, right or wrong. What product will sell, won’t wont. What path makes sense, what path doesn’t. It’s why we have a flood of mediocrity out there – from the movies we watch to the clothes we wear.

Knowing who your customer is can’t come until you know who you are, what it is you’re creating and why. Once you know, you hardmark this information. And then, most importantly, you tune out the algorithm and tune in to people who share your same mindset. It’s a smaller target group than everyone. And that may seem bad, until you realize everyone was never a target group to begin with. Reading this, it all seems logical, maybe even a solid reminder of what you know. But in actuality, enacting it, and following through is not obvious or even simple, but I have created a process for doing it and I share it with you in my book. Almost Reckless isn’t a biography or a story of how I built Tibi. It’s a book gives you the framework of how to break out of the algorithm and move on to your own path to success. Whatever that means to you. And I can tell you from personal experience, once you get there it is incredibly stabilizing.

In the U.S., you can order the book or the audible here: ALMOST RECKLESS

Outside the U.S. order HERE

KNOW THIS: If you LOVE supporting small businesses - which we do - If you go here: Almost Reckless at your neighborhood bookstore then you will feel extra good. I’m shouting out a few of my very favorites here: Athena Books in Old Greenwich, Ct; Bird Bookstore in Dallas, E. Shaver Bookseller in Savannah, Ga and GJ Ford Bookshop on St. Simons Island, Ga. PLEASE IN COMMENTS LET ME NOW YOUR FAVORITE INDEPENDENT BOOKSTORES!!!!

Come with me down my most rabbit hole, I’m sitting here comfortably at the bottom.

I was recently asked: “Would you consider being my mentor?” I get asked that often, usually it’s a college age student. “I want to be someone’s mentor!” is often said to me by someone I’m interviewing or a young eager employee. And I get why. I mean, google “mentor” — who in the hell wouldn’t want one of these people in your life, and what a compliment to be thought of as one.

But the reality?

No one can bear this much responsibility. And even if they could, if they had the time coupled with the will and the skill, this is a set up for failure. One person could never fully offer this to another, you would ultimately always be disappointed. I wanted to dig on this idea further, so I called some friends who sit in c-suites at some positions, those that have arguably “made it.” And I asked if their companies have formal mentoring programs, if they've been mentors to others in a formal capacity, and who do they consider the mentors in their life?

The first two answers were yes. And then second one was far more complicated, because it wasn’t just an individual. And it wasn’t always an actual person. So, I think it’s important to reframe what a mentor is. Why? Because it helps set expectations, it keeps you looking in the right and often unexpected places, and importantly because it allows you to reflect and understand what you are seeking for yourself. And this is the magic combination, learning more about who you are, what you want to do in life, and building a blueprint that helps you get there.

First, let’s give a new visual to a mentor. I think instead of a whole being, it’s going to look more like a Lego piece. And of course, a Lego piece on its own doesn’t say anything, but together they build something - or at a minimum, get you on your way to creating something great. It’s a good exercise to go through, to think what Lego pieces you’ve collected. I’ll deconstruct mine here so I’m clear what I mean. I start first with either what I was seeking or what I found (because time sometimes reveals what we can’t see/articulate in the moment).

1. Principles. My parents, they’ve always lived by them, they were the undercurrent of everything they did and were happy about or maybe even regretted.

2. Empathy, kindness. My sister. Straight up she was always the better person here and I wanted to be more like her.

3. Clarity. My husband. He has a mental toughness about him and it’s saved us in many challenging business and home situations.

4. Possibility. My crazy Great Aunt Tantee. My Grandmother’s sister - she was an entrepreneur, never had kids, had tons of dogs.

5. Confidence. Mrs. Wright and Mrs. Jocoy - when other teachers saw me as an unmitigated disaster, they dug deeper.

6. Worth. Tom Ryder, he was President of my division at American Express. In a sea of Ivey leaguers speaking a language I’d never heard before - he was my beacon - LSU, Dad was postal worker, he is scrappy, large and in charge.

7. Possibility. Hong Kong - the people. An entrepreneurial spirit, it pulls you in.

8. Focus. The movie Nothing In Common. I had no idea advertising was even a thing - once I honed in on a career, my schooling direction fell in place.

9. Work Ethic - my colleagues. There are some that could Master Class this.

10. Tenacity. My boys. I’ve seen them face really big challenges and power through. If they can do it, I can do it.

11. Leadership. Former bosses at Ogilvy and American Express. They didn’t mince words, they explained the why and let me figure out the what. They had courage but humility at the same time.

12. Mindset. I read a lot of biographies, I admire people who are doing some really big things right now and who’ve powered through a lot and have held steadfast in a core set of principles that form a mindset that I share. When I start to doubt, I pull up their book/articles about them. Paula Wallace, the Founder and President of SCAD, Christopher Hitchens, Mary Wells Lawrence, Steve Jobs, Edith Wharton, Al Smith, Andre Agassi. They fuel me.

13. Perspective. My friends I’ve made in my DM’s over the last five years. Never saw that coming, but when I need to bounce an idea, see something through a different lens, they’re now on my speed dial.

There are a few others, of course. BUT I am not complete yet, and I’ve no idea where I will find the next parts that make my final whole.

But here’s an interesting thing of note - there’s not one mentor that I learned MY INDUSTRY from. Maybe that’s because even the industry you pursue, just like your life, is the sum of many parts that are ultimately up to you to put together. This is a helpful exercise to do because it lets you separate what you’re really seeking. Is it just some facts that may help you make a decision or power through a situation - like if you’re a young designer it may be: what should I be paying for this shirt? Have you ever been sued by this predatory lawyer? Is the sell through this Department store asking realistic? Did Saks pay you? Those aren’t mentors, but resources.

So try building your own Lego mentor. See what it tells you, for where you are now, and make sure when it’s speaking that you’re listening. Ok?

And to state what I think may be obvious, this Stack is in no way linked or affiliated with Lego. It’s just a super clear visual.

That sense of fearlessness we had when we were younger seemed hardwired. That almost reckless approach to making decisions that were right for you - unencumbered by expectations and bound by principles that just seemed obvious. Like: don’t do stuff that doesn’t make sense, don’t work with assholes, do or make only what you love and if you don’t love, it make it lovable.

Remember when you tackled life by doing things that just made sense pragmatically and inspired you creatively?

It’s not an accident that the gut gets dulled. Our responsibilities grow, we acquire more to lose, we gain knowledge and start to choke on an algorithm that presents so much certainty about the correct path forward. We begin to question our ability to know the next step, to inherently feel In our gut what is right or wrong. And even worse, we train ourselves to ignore it.

This conversation started in earnest about six years ago now in the closet. The literal closet. I asked people to define themselves in three adjectives. Those three words became a measuring stick for evaluating what was right, wrong, or fixable amongst their wardrobe. It helped narrow the focus for what to buy in the future and it ultimately helped serve to create a visual representation of who we are. Otherwise known as personal style.

The outcome wasn’t just looking good, tho that did happen. What really occurred was people couldn’t help but make logical leaps. When you know who you are, when you can assess a situation, and develop solutions - sometimes perfect sometimes passable - you start applying it to your everyday. When you recognize that you feel smart wearing clothes that convey depth and nuance, when you feel nothingness when everything is too perfect, you recognize the irony of chasing a peer group of people who share only the exact same opinions, or seeking a frictionless environment. Maybe, and in the book I argue pretty strongly, all this agreeableness, or concern of being disagreeable, ends up suppressing the very thing that makes you sharp and enables you chart a course that’s right for you.

Almost Reckless makes a case to trace back and understand who you are, codify your principles and use them as the guardrails to live your life. I’ll show you how I did it - the big leaps I made when I created Tibi, I take you through the years that are highly regrettable but so necessary in the bigger scheme of things to have lived through them, and how we set out on a path that is so uniquely our own. No consultants, industry experts or AI used here. Just our gut coupled with curiosity and a serious work ethic. And most importantly, the book gives you solid tools to help you take action and chart your own course.

Almost Reckless is available now at retailers throughout the U.S., the U.K and some select European locations. If you visit Amysmilovic.com you’ll get more info. I hope you love it, we will have some fun events throughout the year to discuss, and help get you on your way if that’s what you’re looking for. You can also check out The Almost Reckless Podcast on YouTube and Spotify where I have great discussions with varied entrepreneurs, creatives, and individuals who’ve done big things (according to their own measurement) and had guts lost and then found. There’s a common thread to them all - nothing in life is more unsettling than getting pulled off course because we’ve lost our internal compass. It’s what’s caused them to experience failure in life - if you deem failure as chasing a life that is, in the end, not the one you actually wanted.

Almost Reckless will help you find your gut, point your compass. Promise.

Just kidding. And if any one says they do, ignore them. Or hear them out, but their words are just data points, to be either considered or tossed as irrelevant.

I learned this the hard way.

It was the Summer of 2008, and InStyle Magazine was doing a profile on my home. The living room comprised of cold g…

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On my Almost Reckless podcast, I’ve interviewed a range of wildly successful entrepreneurs, executives, and artists. Now “wildly successful” can be subjective, right? And I certainly don’t mean it as framed solely through the lens of monetary rewards or industry recognition - though many I’ve interviewed have had both. Regardless of who’ve I’ve spoke…

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Come with me down my most rabbit hole, I’m sitting here comfortably at the bottom.

I was recently asked: “Would you consider being my mentor?” I get asked that often, usually it’s a college age student. “I want to be someone’s mentor!” is often said to me by someone I’m interviewing or a young eager employee. And I get why. I mean, google “mentor” — who in the hell wouldn’t want one of these people in your life, and what a compliment to be thought of as one.

But the reality?

No one can bear this much responsibility. And even if they could, if they had the time coupled with the will and the skill, this is a set up for failure. One person could never fully offer this to another, you would ultimately always be disappointed. I wanted to dig on this idea further, so I called some friends who sit in c-suites at some positions, those that have arguably “made it.” And I asked if their companies have formal mentoring programs, if they've been mentors to others in a formal capacity, and who do they consider the mentors in their life?

The first two answers were yes. And then second one was far more complicated, because it wasn’t just an individual. And it wasn’t always an actual person. So, I think it’s important to reframe what a mentor is. Why? Because it helps set expectations, it keeps you looking in the right and often unexpected places, and importantly because it allows you to reflect and understand what you are seeking for yourself. And this is the magic combination, learning more about who you are, what you want to do in life, and building a blueprint that helps you get there.

First, let’s give a new visual to a mentor. I think instead of a hole being, it’s going to look more like a Lego piece. And of course, a Lego piece on its own doesn’t say anything, but together they build something - or at a minimum, get you on your way to creating something great. It’s a good exercise to go through, to think what Lego pieces you’ve collected. I’ll deconstruct mine here so I’m clear what I mean. I start first with either what I was seeking or what I found (because time sometimes reveals what we can’t see/articulate in the moment).

1. Principles. My parents, they’ve always lived by them, they were the undercurrent of everything they did and were happy about or maybe even regretted.

2. Empathy, kindness. My sister. Straight up she was always the better person here and I wanted to be more like her.

3. Clarity. My husband. He has a mental toughness about him and it’s saved us in many challenging business and home situations.

4. Possibility. My crazy Great Aunt Tantee. My Grandmother’s sister - she was an entrepreneur, never had kids, had tons of dogs.

5. Confidence. Mrs. Wright and Mrs. Jocoy - when other teachers saw me as an unmitigated disaster, they dug deeper.

6. Worth. Tom Ryder, he was President of my division at American Express. In a sea of Ivey leaguers speaking a language I’d never heard before - he was my beacon - LSU, Dad was postal worker, he is scrappy, large and in charge.

7. Possibility. Hong Kong - the people. An entrepreneurial spirit, it pulls you in.

8. Focus. The movie Nothing In Common. I had no idea advertising was even a thing - once I honed in on a career, my schooling direction fell in place.

9. Work Ethic - my colleagues. There are some that could Master Class this.

10. Tenacity. My boys. I’ve seen them face really big challenges and power through. If they can do it, I can do it.

11. Leadership. Former bosses at Ogilvy and American Express. They didn’t mince words, they explained the why and let me figure out the what. They had courage but humility at the same time.

12. Mindset. I read a lot of biographies, I admire people who are doing some really big things right now and who’ve powered through a lot and have held steadfast in a core set of principles that form a mindset that I share. When I start to doubt, I pull up their book/articles about them. Paula Wallace, the Founder and President of SCAD, Christopher Hitchens, Mary Wells Lawrence, Steve Jobs, Edith Wharton, Al Smith, Andre Agassi. They fuel me.

13. Perspective. My friends I’ve made in my DM’s over the last five years. Never saw that coming, but when I need to bounce an idea, see something through a different lens, they’re now on my speed dial.

There are a few others, of course. BUT I am not complete yet, and I’ve no idea where I will find the next parts that make my final whole.

But here’s an interesting thing of note - there’s not one mentor that I learned MY INDUSTRY from. Maybe that’s because even the industry you pursue, just like your life, is the sum of many parts that are ultimately up to you to put together. This is a helpful exercise to do because it lets you separate what you’re really seeking. Is it just some facts that may help you make a decision or power through a situation - like if you’re a young designer it may be: what should I be paying for this shirt? Have you ever been sued by this predatory lawyer? Is the sell through this Department store asking realistic? Did Saks pay you? Those aren’t mentors, but resources.

So try building your own Lego mentor. See what it tells you, for where you are now, and make sure when it’s speaking that you’re listening. Ok?

And to state what I think may be obvious, this Stack is in no way linked or affiliated with Lego. It’s just a super clear visual.

Do you now when to stop? It’s a loaded question, allow me to frame it so you can understand what I mean.

At dinner recently, my friend Amy G. who is EVP Head of Programming at HBO (there are other elements to her title way to long to lay out here), was asked by a Gen Z member at the table: “Did you always have this in your goals, to be where you are to…

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Years ago I began sermonizing that a bifurcated closet sucks. The initial…

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Reason number three: the algorithm isn’t the plan and it definitely doesn’t (shouldn’t) build your path.

Back in the day……before there was an algorithm, the common refrain bleated at me from industry experts was: “this is how it’s done. Period.” Often this made no sense to me, but who was I to contradict - after all, these are “experts”. Fast forward…

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Because a bifurcated life sucks.

I’ve spoken often about a bifurcated wardrobe, how it makes you feel disjointed when you’ve separated the daily moments of your life - you never feel quite whole. When you’re visually one person from 9-6, another at night, another on the weekend it can mess with the understanding of who you are. Turns out this mindse…

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In no particular order, reason number one:

I just finished Apple tv’s Mr. Scorsese, and I’m captivated. These types of docs get me every time. This one like so many takes me in to the mindset of someone so very deeply passionate about his craft, a true genius, but who’s ultimately plagued by much of the same that afflicts others with this level intensi…

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