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I Burned My Career to the Ground (3 Times): How To Start Your Career Over After Failing


“We would like to offer you two week’s salary if you just leave now.” That’s what the head of HR said to me after my third career fail. Yup, third time wasn’t the charm.


On paper I was a failure. I looked like your typical millennial career hopper. No clear direction of what to do next. No idea what to be whenever I decided to grow up. No income.


I failed epically in the traditional career trajectory, but each lesson learned was invaluable to where I am now. And this year I will cross over into the six-figure millennial club (that’s right, suck it 2020!)! I share my lessons learned so you can enjoy the success, sans the public humiliation.


Career Fail 1: Working for my Father

Now, this is not a failure in idea alone. I was about to graduate college with a degree in Psychology and a minor in Economics Management. I knew I wanted to work in business but I wanted to come at it from a different angle. I wanted to understand how people think in order to sell them sh*t. *shrugs*


I had already worked with my Dad’s company over some summers throughout college. I was doing more administrative tasks but we both had big hopes for me and doing marketing for his business. Neither of us were prepared to balance a really solid Father/Daughter relationship and a Boss/Employee one.


I thought I was the sh*t. I did not take direction well. I did my job really well, don’t get me wrong, but I was probably not the easiest person to manage and I credit that to my boss being my Dad. I would’ve learned the game that is advancing your career better if I was served a slice of humble pie by someone I knew I couldn’t talk back to. Also, tell someone you work for a parent and they automatically assume you don't do much.


When my boyfriend and I decided to quit our jobs and move to NYC (seriously don’t recommend this for everyone… It was risky but did yield us that high reward in the end!) I was 3 years into my professional career and was zero percent ready for what was next.


Career Fail 2: Real Life, Devil Wears Prada

Enter the fail that no one would argue is anything but that. I hit the ground running when we moved to NYC. I had meetings with recruiters stacked, I sent out 15 resumes a day, I had 3 phone interviews I scored myself. It was a lot in a very short amount of time- I have always been good at job hunting.


After only a week of looking I was offered a job and I took it. I didn’t negotiate at all and I was told I had 5 minutes to decide if I would take it. Sweet little, naive Kristen took the job. I remember even thinking if I lasted a year that would be nice. I could tell from the very first time I entered this office that it was not a healthy environment. But it was glamorous!


I signed something making it so I can never really spill the tea on this place, but it was some real life Devil Wears Prada sh*t. Just put this info in your back pocket should you need it: being told that meals were provided for you and there was a car service to take you home if you worked past a certain hour could be signs to RUN. Sounds lovely, but it means you NEVER stop working.


I was finally served a bakery’s worth of humble pie and after 6 months I broke down in tears and quit on the job. My boyfriend came home, like the angel he is, with a big bottle of vodka to celebrate not going to that place any more. But that didn’t heal the humiliation of rage quitting a job after only 6 months. NYC is f***ing tough to newcomers and I was seriously afraid I couldn’t make it here.


Career Fail 3: The Quarter Life Crisis/Mental Health Meltdown

But after fleeing the toxic workplace, mascara running from crying so much, I mustered up the energy to hunt for a new job. I took more time to find a better environment and a calmer fit for me. After 4 months I landed what I thought was my dream job.


I worked on the 22nd floor in Midtown Manhattan. I watched little minions line up for the big New Year’s Eve disaster of an event from the comfort of my office in the sky. I was at a place that was so stereotypically climb-the-corporate-ladder. But I loved it, for a while.


What I learned here was the game. The office politics behind rising in your career which often times meant stomping on others (even though that part was really unnecessary). I watched men I respected and were mentors to me cheat on their wives regularly. I watched what not so great economic times does to managers that are afraid of losing their own jobs.


I lasted a year this time. I always knew I had bad anxiety but it turns out I’m bipolar. Yeah, untreated bipolar in this environment is not a great mixture. My boss and I became combative with each other (him dealing with the not good economic times thing and me dealing with a manic episode is not a good cocktail. 0/10, do not recommend). I thought it was a GREAT idea to put in my notice in by writing a novel, emailing it to my boss, and cc’ing HR. HA!


He called me into his office. Long story short I had an extreme panic attack in front of him and left his office with mascara running, once again, and hid in the bathroom for hours (or what felt like hours). HR called me, because my boss was in the wrong over a lot but I was an overly dramatic twat in need of a lot of medicine, and by the end of the call they offered me my two weeks pay if I would just not come back.


Quitting a job because of toxic environments is a good thing. Rage quitting and burning almost every single bridge along the way… VERY BAD!


All of this turned out to be a huge blessing in disguise kind of thing because it did lead me to get diagnosed and spend a couple years getting my mental health on track. Mental health = good. Derailing your career = bad. Welcome to 27, kids!


Bonus- Career Swerve! Now My Resume Makes No Sense

Part of how I got diagnosed as actually crazy was the fact that I started my own life coaching business while working full time. I was manic and never slept, but hey I at least somehow set myself up to earn enough money to pay my portion of the rent.


I then set up a GoFundMe to get my yoga teaching certification. People can be really amazing and a lot of people pitched in to help me out with this.


So I went from climbing the golden corporate ladder, to mental breakdown to the max, to life coach (still seems ironic to me looking back but I did help a lot of people out too!) and a yoga teacher. I have 2.5 years of what my psychiatrist calls being underemployed and is a very interesting blip on my resume.


Lessons Learned: Three things I learned I need in a career:

While I gained two realllllllllllly embarrassing career endings and one that people dismissed as just me working for my Father and not a “real job”, I also learned what would help me thrive back in the more traditional workforce.


1- The office environment had to 100% be healthy for my mental health. I knew that jobs asking for 24/7 availability were not for me. Typically this removed jobs requiring suits. You can tell when you walk into an office the vibe and I learned to trust my gut. Where I landed, and where I am today, was an interview full of casual conversation and people accepting this really ambitious girl who happened to have some rose gold hair at the time and a nose stud. Those things also help eliminate toxic workplaces!


2- I needed a job that had a lot of potential. WTF do I mean by this? I needed a job vague enough that I could take on more as I found it and wasn’t told to stay in my lane/that’s not my business. I didn’t care about the job title, I cared about the potential to explore and not be told no because of office politics. Being told no doesn’t have a good history with me and bosses…


This job was a new creation for this office and had a lot of room for creativity in how to execute the responsibilities. Perf.


*Side note: in an interview please please please don’t ask about your future job in that company and have the interviewer see you are already bored with the job you don’t even have yet. Ask questions about the day to day aspects of the role, or what visions the interviewer has for the job. This will tell you about the potential of your role without talking yourself out of the job.*


3- I needed an income that brought me some pride. Yeah, yeah, yeah. “Money can’t make you happy!!!!!” Bullsh*t. Money makes me very happy and so does the idea that I can be 100% financially independent even if I don’t need to be. Always ask for more, even if what is offered is something you are very okay with accepting. I love money.


Career Win: How I’ll Make My First Six-Figure Year

What a f***ing journey. Three career fails, an extremely random career blip (that in some ways is still alive today, hence this whole website), and finally a happily ever after with a job that I actually do really like. I kissed a lot of frogs, but because I kept getting back up again and fighting for the idea I could be successful I was able to land in a pretty great spot professionally. Keeping my manically made business going to a certain degree and working at a job and with people that are pretty awesome is going to make 2020 my first six figure year.


While all that I have written above focuses on my failures, it does not even begin to tell you the other side of the story: the one where I bust my a** at every job I've ever had. We get so wrapped up in the failures that we forget to present ourselves to others, especially in a job hunting scenario, in a positive light.


I had a strike against me for "job hopping". I looked like I got bored easily and skipped around but I was able to say that I was exploring what I really wanted in a career and now I have a clear picture of what that is and I'm looking for my long term company. I couldn't really explain my mental health breakdown, but I did explain that I was sick and needed to leave a job to deal with an illness that is 100% fine now.


You have a choice: you can shrug when people ask you about things that make you insecure on a resume or you can use them to your advantage. Presentation is everything.


The biggest lesson here, kids, is that you can have a killer resume and out interview all the career fails you may have had. How you present yourself on paper, and in an interview, is significantly more important than you feeling like a failure. It takes some strategy and a lot of hard work but if I can do it anyone can (or whatever other inspirational poster sh*t works for you).


Want to learn to write a resume that is guaranteed to get you, yes even you, an interview??? Click here to learn more.


Fun fact: some studies have shown that failing early in your career will make you more successful. Cool beans. Read about that here.


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