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It’s Never Too Late: 3 Women on Second Chances and Changing Careers
11.28.17

In partnership with Tamara Mellon

Doesn’t this sound weird? I used to not know that you could switch careers. I thought you were locked into your trade from the moment a hand was shook upon it. You’re going to school to be a doctor? Have fun being one forever! Oh, you’re interested in baking? Better pray you never develop a gluten allergy. I thought this until I finally started meeting women who’d done it — inspiring women, brave women, brazen women. And then I did it. Later, I watched in admiration as my own mom, around the age of 55, forged an entirely new path, further enforcing that there’s no such thing as “stuck,” or “too late.” Second chances, it turns out, are there to be grabbed.

(So are third chances, fourth chances, fifth chances…)

Tamara Mellon, the former co-founder and CCO of Jimmy Choo, took her chance when she pivoted careers and left a household brand to start a footwear line for confident women under her own name. She knows the high value of a smart risk that comes from the goodness of your gut. Over the last three months, in partnership with Mellon and her shoes, we profiled women who, as Haley put it, “may not ‘have it all,’ but who contain enough multitudes to prove that mission unworthy in the first place.” In this final installment, I spoke to three women who took a leap of faith in themselves, women who exited the careers they knew for one that called to them so loudly it was impossible to ignore.


Polly Rodriguez, 30, CEO of Unbound

Polly left her position at Deloitte Consulting to begin Unbound, a sexual lifestyle company aimed at empowering women through sexual exploration.

Tamara Mellon shoes styled with Topshop suit and Safsafu earrings

If you could break up all the important, pivotal “adult” phases in your life into chapters, how would you title them?

Chapter 1) Wait, I Don’t Remember Asking for a Poo Bag? Cancer at 21
Chapter 2) I’m Like a Total Expert in Anthrax Now: My First Job on Capitol Hill
Chapter 3) Cancer Didn’t Kill Me but Business Casual Might! Strategy Consulting on Wall St.
Chapter 4) So Are the Women Allowed to Hold the Conch Shell Yet or Nah? A Crash Course in Startups
Chapter 5) Selling Vibrators in a Condemned Coworking Space Above M&M World, Have I Thrown My Career in a Trash Can? Stay Tuned…

Which one are you in right this moment?

I’m somewhere between working above M&M World and wearing business casual, both physically and emotionally. There will always be a part of Unbound that feels scrappy and imperfect, but I think we all kind of like it that way. We’re professional yet unpolished.

Tamara Mellon shoes styled with Topshop suit, The Wing T-shirt and Safsafu earrings

What was the moment of clarity that made you realize it was time to pivot your life/career from the one you knew?

For me there were two really poignant moments in my career that made me ask myself what the hell I was doing with my life.

The first was moment was the transition from consulting to the startup world. I was crying alone in the office at 10 p.m. I had missed my best friend’s birthday to make a pitch deck about why low income patients should pay for brand name drugs instead of the cheaper generic option. I realized that I had become a part of the system and was disgusted with where my priorities were in that moment.

The second moment was the transition from working at someone else’s startup to working on my own. I was ordering fruit fly traps IN BULK on Amazon. The women in the office, tired of cleaning up after every single team lunch, decided they would stop and see what happens. Well, lemme tell ya, fruit flies are what happened. And a massive amount of them. It was that moment that I realized: I am done working for young boys who cannot even throw their food away. It’s time to build something of my own.

What was the very first actual step you took and how did you feel? How did you get through those emotions?

I got fired from my last startup via Google hangout in a Starbucks on my way to a doctor’s appointment. Like I literally had to get out of the cab and walk into a coffee shop with free wifi so that I could be let go. So, that didn’t feel great, but it ended up being the best thing that could have ever happened to me. At first it was terrifying, but then it was liberating to realize that I had a fresh start. Change is hard, and sometimes you need someone to light the fire under your ass to get to work.

How did you know that what you were doing was the right thing?

In order to be a successful entrepreneur, you have to enjoy constantly being in over your head. There’s this sweet spot between, “I GOT THIS!!!” and “…Holy shit, I’m gonna barf” that you live in every single day. You also have to be obsessed with getting feedback from people who will tell you the truth. For Unbound, I got my friends who had never owned a vibrator before to try one. Every single person was obsessed with the products after they used them, and that was how I knew we were onto something.

I also think that, sometimes, you can just feel it in your bones. I could so clearly see what Unbound was destined to become and how it could be so much more than just selling products, but really giving women a sense of entitlement to enjoy their bodies.

I think there’s an age bias around when you can/can’t pivot in your life. Are you able to speak to that? Any other sort of biases you’d like to address?

I think biases are baloney (or bologna if Mrs. Cleveland from Parkway Central High School is out there reading this right now). Most of the time, those who project their bias on you are jealous because they don’t have the gumption to take a risk themselves, so they question why you’re doing it and try to make you feel stupid about it. I got over that feeling a long time ago, but I don’t deny that the judgement is real. It’s up to you whether or not you choose to acknowledge it.

Tamara Mellon shoes styled with Topshop suit and Safsafu earrings

How did you find people who supported you? How did you ignore those who didn’t?

Going through cancer weeded out a lot of people in my life who were just taking up space. I got really lucky with my family and friends who never gave up on me. My best friend Sari helped me pay rent, my parents took money out of their savings, my hometown best friends Ryan and Kelly sold their Jeep to invest in Unbound. There were people all along the way who gave without asking for anything in return.

How did you take learnings from your “past chapters” and apply them to your current chapter?

Cancer taught me that nothing good ever comes from fear.
Working for Senator Claire McCaskill taught me to fight for what you believe in and never apologize for it.
Consulting taught me that pedigrees mean nothing and work ethic means everything.
Working at a YCombinator startup taught me that done is better than perfect.
Unbound has shown me that determined women can change the world.

What actionable advice can you give to someone who wants to make their own life change — beyond the gold standard “believe in yourself?”

Roll up your sleeves and learn as much as you can about what you’re interested in. Tactically, this most often involves Google-researching the companies and industries you’re interested in, followed up by LinkedIn stalking any potential connections you have. Find out if crazy cousin Marty from Florida will introduce you to his friend who started that wine company. Reach out to the company you admire and offer to volunteer at their next event. Be relentless and fearless about learning as much as you can. That’s the only way you’ll find out if the leap is worth it.

Tamara Mellon shoes styled with Topshop suit, The Wing T-shirt and Safsafu earrings

Karen Young, 39, CEO & Founder of Oui Shave

Karen left her job as the manager of a major beauty company to start Oui Shave, the first modern shaving experience for women

Tamara Mellon boots styled with Desmond & Dempsey robe and Roxanne Assoulin earrings

If you could break up all the important, pivotal “adult” phases in your life into chapters, how would you break them up?

Chapter 1) College: Ramen & Freedom
College isn’t necessarily adulthood for many, but for me, it marked the time I fled my nest and didn’t look back. I didn’t have the healthiest relationship with my mother, and I took my strong will and “can-do” attitude and went off in search of myself. One case of mono, many packs of ramen and sweet, sweet freedom.

Chapter 2) Divorce: I Know (Not) What I Am Doing
Let’s skip the marriage part because that decision wasn’t terribly remarkable. I was young, in love, and I was a fully formed adult. Ha. What no one tells you is how hard it is to figure out what healthy love looks, feels and sounds like. Is it supposed to hurt? Like…big hurt or a series of small hurts? My divorce brought some of that freedom I was always seeking, lots o’ cake, and my foray into online dating. Swipe left.

Tamara Mellon boots styled with Desmond & Dempsey robe and Roxanne Assoulin earrings

Chapter 3) New Friends: What About Your Friends?
Adult female friendships are a godsend. Post-divorce I found that I needed a new set of friends who weren’t married, with kids, living in the suburbs. These were the women I turned to for real conversations about dating, working and life in general. My girlfriend-ships are low in quantity, high in quality.

Chapter 4) All Grown Up: Choice Is a Privilege
I probably made the most active, conscious, full-hearted choice by being in my current relationship. I decided how I wanted to be treated and when the guy came along that did that well, I said yes. I am surrounded by good, kind, supportive, caring people, and I realize that I am privileged to actively make that choice. I made the choice to work for myself and I am also privileged to make that choice.

Which one are you in right this moment?

Currently, All Grown Up.

What was the moment of clarity that made you realize it was time to pivot your life/career from the one you knew?

My moment of clarity came over the course of a few months when, each day, I sat at my desk and felt less and less like the creative, thoughtful, enterprising woman I’ve come to know myself to be. I was eating just to feel full, having surface-level interactions, and I felt the kind of tired that can only result from sheer boredom. I was on a flight back from a family trip and everything in my body said “no more.” So I gathered my courage and said, “Okay, no more.” I quit my job the next day.

What was the very first actual step you took and how did you feel? How did you get through those emotions?

Because I went into business for myself while still working at my old job, I set aside six months of “runway” to cover rent, personal expenses and the business’ expenses. I was already operating profitably so I took a chance that I could replicate that over the next year. I had originally hoped to save up a full year of runway before leaving, but my business was growing at a clip and I was exhausted, so I left the cushy job earlier than expected.

If you’ve ever ridden a rollercoaster, that feeling when you’re at the very top and the ride suspends for a second in mid-air before a free fall, that is the feeling of quitting your cushy 9-5 job. It’s a mixture of exhilaration and the desire to hurl. Exhilahurl? I relied on my fiancé, my family, and my girlfriends to get me through those emotions. They had faith in me that I, at times, didn’t have in myself. They were my first customers and my cheerleaders and saw something bigger than I allowed myself to see at the time.

How did you know that what you were doing was the right thing?

Entrepreneurship is a mental challenge that transitions quickly from “I’m brilliant!” to “WTF am I doing?” and back. Founder’s Whiplash. This time I knew I was doing the right thing because I heard it from my customers: every email about their “life-changing” experiences with the products got me through tough times. I use that feedback to develop and grow the brand as well as push myself forward. I rely on our customers to help determine the real value of the company, beyond the products, and that validation is the utmost clarity for what I should be doing.

I think there’s an age bias around when you can/can’t pivot in your life. Are you able to speak to that? Any other sort of biases you’d like to address?

Tamara Mellon boots styled with Desmond & Dempsey robe and Roxanne Assoulin earrings

I can’t say I’ve experienced an age bias, but I’ve not been affected by thoughts about my own age or the perception of my age very much. Not yet, anyway. I do worry about bias as a black woman, raising venture capital, who doesn’t fit the traditional mold of fundable founders. The statistics on female founders who receive venture capital are dismal, and black female founders almost non-existent. I wouldn’t be here if I didn’t know how to trample a good bias, however.

How did you find people who supported you? How did you ignore those who didn’t?

I have found in the last few years that people seem to be in two camps: those who support entrepreneurship, and those who do not. The former are usually entrepreneurs and I made sure to find groups of them wherever I could: Twitter, Facebook, in person. I think if you see it this way, it becomes less personal. Ignoring those who don’t support you isn’t always easy, as they’re often family or friends. Relegate non-business conversations to those who don’t.

How did you take learnings from your “past chapters” and apply them to your current chapter?

All of those chapters have snowballed into the person I am today and I’m ever grateful. To me, it would be impossible to drop those learnings, but I do think it helped to develop my gut instinct.

What actionable advice can you give to someone who wants to make her own life change, beyond the gold standard “believe in yourself?”

Once a year, sometimes twice if I’m extra motivated, I like to map out what I’d like my life to look like that year. Where do I want to travel? What would I like to be more skilled at? What does my best health look like? If that sounds overwhelming, map out just one thing over the course of six months and see how your life changes. Then put it someplace you’ll see it often. I place mine behind my front door. It’s pretty powerful to see how much impact your action, or inaction, has on your life.

Tamara Mellon boots styled with Desmond & Dempsey robe and Roxanne Assoulin earrings

Katie Sturino, 33, Founder of Megababe, Author of The 12ish Style

Katie Sturino, former publicist, left her own public relations firm to start a body positive fashion blog and problem-solving beauty product line for women

Tamara Mellon shoes, Kenzo skirt, Monogram T-shirt, Hysteria by Happy Socks, Roxanne Assoulin necklaces

If you could break up all the important, pivotal “adult” phases in your life into chapters, how would you title them — or how would you break them up?

Chapter 1) The Hiding Behind Sunglasses Years: I was just out of college and trying to navigate adulthood.
Chapter 2) Tinder PR: I took a step out on my own to build a small fashion publicity firm (which was just two people, sometimes).
Chapter 3) The Living Your Dream Phase: I’m inspiring women to accept themselves, writing about what I wear, rescuing dogs, stopping thigh chafe…it’s wonderful.

Which one are you in right this moment?

THE LIVING YOUR DREAM PHASE!

Tamara Mellon shoes, Kenzo skirt, Monogram T-shirt, Hysteria by Happy Socks, Roxanne Assoulin necklaces

What was the moment of clarity that made you realize it was time to pivot your life/career from the one you know?

After years in public relations where it was my job to garner attention around my clients’ brands, to sell them, to work with press, I felt the immediate ease with which media responded to my mission. They welcomed it as though they’d been waiting for someone to do this. The more and more positive feedback I received, the more sure I was that the 12ish Style was my future.

What was the very first actual step you took and how did you feel? How did you get through those emotions?

I retired from doing PR after nine years, which meant saying goodbye to clients I had been with for years who felt like family. It was a total risk to say I believed in what I had to say so much that I was willing to risk financial security and leave behind a steady business that I enjoyed, but I had to try.

How did you know that what you were doing was the right thing?

Every once in awhile, the universe (or something) aligns with your plan. That’s what happened to me. There was momentum and energy almost immediately for the 12ish Style so I knew it felt right. That didn’t make it easy, and I still have moments of, “What the hell am I doing,” but as my friend Carole Radziwill said to me, “Ride in the direction the horse is moving.”

Connecting with so many cool women who share their stories of learning to accept and celebrate their bodies has been the real amazing part of this journey so far.

Tamara Mellon shoes, Hysteria by Happy Socks

I think there’s an age bias around when you can/can’t pivot in your life. Are you able to speak to that? Any other sort of biases you’d like to address?

It was my own bias: I thought my life was supposed to be lined up perfectly — it varies from person to person but usually it’s a lofty, unrealistic list of comparisons — by age 29. But then you turn 30 and realize you can barely figure out how to separate your laundry. There’s this notion that everyone must achieve everything immediately, that you cannot switch lanes if you have chosen a certain path. If you are willing to be humble and learn, I think you can do anything. I was a publicist for nine years and still couldn’t predict what would come next. At 27 I thought I’d be in PR forever. I never imagined that this was my next move, but I stayed open to the opportunities that came to me and went toward what felt right.

How did you find people who supported you? How did you ignore those who didn’t?

I learned to seek advice from those who I trust and to quickly vibe out those who are not looking out for my best interest. I consulted the head of a major agency before I began The 12ish and she told me it was a mistake to get started so late the game. But I didn’t listen. I knew I had something to offer that wasn’t out there yet.

How did you take learnings from your “past chapters” and apply them to your current chapter?

Tamara Mellon shoes, Kenzo skirt, Monogram T-shirt, Hysteria by Happy Socks, Roxanne Assoulin necklaces

My life as a publicist has given me such helpful insight as a beauty entrepreneur and blogger. I feel like I have been on both sides of the industry.

What actionable advice can you give to someone who wants to make their own life change — beyond the gold standard “believe in yourself?”

Speak up and take every opportunity that feels good in your gut. I knew I wanted a change about two years before it happened. I started talking to my therapist and making lists of jobs I might want to do. I wanted to open an ice cream shop for a while but then realized I didn’t like the day-to-day life of a retail owner. I ran through a lot of jobs in my head I thought might be a fit but after speaking with people who did them, I was like, Nope not for me.

While still in PR, I decided I wanted to make my dog Toast famous, which was not a real job, but it meant I got to rescue dogs. Toast was later invited to a NARS shoot for Man Repeller. I met Amelia Diamond on set and said to her, “You know, I never see people with my body type on Man Repeller.” A few weeks later we did a story together for the site. The comments were all so supportive. It was validating.

I started 12ish Style shortly after, and then I started Megababe. It all flows if you keep your eyes peeled, listen to yourself and stay determined.

Tamara Mellon shoes, Kenzo skirt, Monogram T-shirt, Hysteria by Happy Socks, Roxanne Assoulin necklaces

Photos by Aaron Richter. Special thanks to Sid Gold’s Request Room.

The Spotlight and Tinsel styles are exclusively available on pre-order for all Man Repeller readers.

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