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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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  • Nina

    love Unbound!! polly is so inspiring and their store is BOMB AF

  • amelie

    This is so inspiring. I’m soon graduating college, got offered a fulltime job at the company I currently work 8h a week at, but I’m pretty sure I’ll be miserable there. So I’m also (thinking of) starting my own business. 🙂

    And damn, that pink suit is love.

  • Paola

    No one having gone from Industrial Engineering to Fashion Design? I need a role model. …or should just work really hard to become my own role model.

    • Amelia Diamond

      we’ll search while you work on that then get back to us so we can sound the alarm!! can’t wait to see what you design.

      • Paola

        this warms my heart!

    • additionalmayonnaise

      Misha Nonoo went from business school to fashion design!

  • Kristin

    So inspiring! But I would have liked to have heard from your mom. Or someone else in past their 30’s—you are supposed to change directions in your 20’s, no?

    • Rebecca Harkin

      Agree! I’m in my 50’s and it is a harsh world out there just trying to line up an internship in my new chosen field. I suppose there is no expiration date on becoming an entrepreneur since you are hiring yourself, but if seeking to work for someone else, expect a ton of age bias.

    • Amelia Diamond

      my mom is quoted in this story! https://www.manrepeller.com/2017/11/life-advice-from-women.html

      *but totally – we will continue to speak with a range of women of all ages about career! (if you feel like reading someone who…has been in her career forever! who’s a grandmother, this is a good read: https://www.manrepeller.com/2017/11/women-in-science.html)

  • What an awesome group! I am so inspired.

  • Aleda Johnson

    I love how Karen actually talked about the nitty-gritty financial details. I see too many of these inspiring stories where someone up and quits their job to start a new career. Bills still have to be paid!

    • Amelia Diamond

      totally!

  • Imaiya Ravichandran

    omg polly is HILARIOUS

  • Jam Jam

    The last ‘real’ job I had was with suits and loads of depressing business casual – I just wore a lot of leather mini skirts and heavy eyeliner. Style is the best middle finger salute before you peace out of office life for good!

  • ByeBeckz

    This was wonderful!!

  • Julie Randall

    Omg, how to explain how fast I bolted to ebay to find those sold out pink velvet pants? Oh yeah.

    Also, high-five, career changers! I graduated 15 years ago with an art history degree and just went back to do a premed program!

    • mandy

      I’d love to hear your story!

      • Julie Randall

        Oh thanks!! Basically after working as a wedding/portrait photographer for several years I was super burned out, and in that time I had also had two kids and ended up being the default stay-at-home parent, which wasn’t a good fit for me. I started thinking about what I could do with my existing experience/education, and nothing sounded interesting until I removed the self-imposed back-to-School limit for myself. As soon as I allowed that possibility, it felt really right. I’m not one hundred percent sure which area of medicine I’ll end up in (right now neurology and women’s health are at the top), but I’m really excited about the different options I’ll have, which feels amazing.

        • Amelia Diamond

          this is so cool!!

  • Chelle

    Loveee how candid they each were in discussing their sacrifices, external support systems (or lack thereof) and internal doubts they faced along the way

  • Elisabeth Austin

    Under-employed at an Airline at 36, holding the largest internally flawless diamond in the world at 39. BigSwingingRock.com DiamondRunway.com

  • Abigail Thacher

    I liked this article, but all three stories really only discussed career changes in the business world. It would have been instructive to include someone who worked in a medical field, law, etc.

    • Amelia Diamond

      Someone mentioend that below! Career is something you’ll continue to read lots about on Man Repeller, which means all sorts of jobs/careers/paths.

  • Jolanda

    Can I say I really liked the interview questions? I am not an expert in any way, and my career change was a lot less dramatic, but reading these interviews still made me feel inspired, and made me question how I would answer some of the questions, myself. My favourite is: How did you take learnings from your “past chapters” and
    apply them to your current chapter?

    • Amelia Diamond

      how would you answer??

  • Hil

    I loved reading this and appreciate their stories and insights BUT they all switched from one kind of business to starting their own business. Definitely a big deal but it seemed more about becoming an entrepreneur than really a full blown career change. Anyone starting a business has a job to leave. It makes me think it must be a lot more rare to switch fields, like going from a political science professor to a tv writer or a lawyer to a baker. Once you’ve invested that much time and money into training it can really lock you in.

    • Amelia Diamond

      I would argue that their self-started businesses *were* career changes in that all of them are in new fields than they were before — but I get it, drastic changes (lawyer to a baker, for example) is a whole different conversation. Will think on this! Would love to explore women who’ve gone these routes on MR!

    • imeansure

      Yep, I would be into that. I have no desire to start my own business and I honestly think it can be a pretty unrealistic option for most people, so I’d like to see other stories like what you mentioned

  • Bummed

    This article is great, definitely an inspiring message. However, I don’t understand why Katie would be lying about her age. I know her personally and I know she’s 37 (or 38? We’re the same age, girl.) I can’t help but think how disengenuous it is for her entire brand (and manrepeller’s for that matter) to be built on acceptance and to be lying on multiple fronts now. Katie, I’ve seen your age as younger than you are on multiple articles now. I respect you on a business level, but this is not cool. Be yourself.

  • elpug

    ok but how do you even figure out what you want to do in the first place? i’ve gone from environmental science degree to waiting in limbo working retail until i find the right job that strikes my passion. i’m afraid i’ll have waited too long since graduation that i won’t be relevant anymore. i’d love to start my own business too but where do you even begin?!

    cue existential crisis

  • Anetra Houston-Gilbert

    Oh my God I love women! Only we can get down to the ends and outs and Nitty Gritty of the business world and still gush over a bomb pantsuit! LOL

  • Melanie Gershman

    love this

  • Kiara Holt

    This article touched my soul literally! I’ve been finding it so difficult to accept that my dreams of becoming a major fashion stylist will not be what I imagine. I’ve always had an appreciation for the technology industry but sometimes we aren’t paying attention to the signs that are in our face. This yea, I found myself at a tech startup! I am now studying how to become a UX/UI designer! I love every minute of it. Oddly, enough there is a fashion tech community and I now have a blog that focuses on fashion and tech! Change can be scary yet so good! Thank you Ameilia this hit home I loved it so much I feel many women in tech would appreciate this I posted it on my blog. Thank you!

    http://www.hoodiesanheels.com/

  • Kate

    Omg I needed this article so much right now! I just turned 30 and quit my cushy 9-5 job to move across the country. I’ve been saving up and making a huge leap – know these feelings all too well. I can’t even tell you all the negative comments I’ve heard, but I know I need this move to figure out what I’m passionate about and what career I DO want to do. I’ve lost the fiery hard working side of myself and I realized it was from sitting in a cube all day. I’m so terrified and excited to be starting a completely different life for the New Year. This makes me feel less scared and that things will work themselves out.