The (Real) Story So Far
In the professional world, there is an emphasis on branding yourself, and on your ability to tell (read: sell) your story in a way that demonstrates your unique value. All sorts of effort goes into this. Your social media content, your profile photos, professional accomplishments, developing your “voice”. “As employees become more transient and separate themselves from their employers, their individual ‘brand’ and story becomes ever more important” the theory goes. Developing your brand helps you get and keep jobs.
Hell, I created this Medium account to do that. I wanted potential employers to see that I was smart, articulate, and thoughtful about more than what my work history has entailed to this point.
Of the many exhausting and frustrating things about job hunting, this facade you must create and maintain for yourself is definitely one of them. Your resume is your professional highlights and mentions none of the struggles or downfalls along the way. Your LinkedIn is a more interactive and colorful version of the same accomplishments. Your social media accounts are a curated image of your fun side. Show them all of your good sides, and none of your bad.
I am exhausted and frustrated by this. I’m tired of having to try to spin the difficult parts of my life as some glorified learning experience that I can apply to a company to help their profit margins. Vulnerability is freedom, you put your true self out there and accept whatever reaction you get. Happiness is accepting reality on reality’s terms. So with that in mind, here is my full career story to date, with all of the ugly details that everyone will tell you to hide.
Let’s start in 2014, Junior year of college at Wake Forest.
I spent the first half of the year in Prague studying abroad through NYU. I’m having a lot of fun and doing the full immersion thing, not thinking about my professional future or internships that would start in 8 months. Spring break rolls around and everyone else is finding internships that will set them up for jobs after graduation. Cool, I’m on it.
This is the first time I’ve applied for work outside of the restaurants and hotels of Myrtle Beach, so I really don’t know what I’m doing. I’m feeling good about myself though, so I apply for these (unbeknownst to me) highly competitive internships in DC. Intern for the Senate Committee on Foreign Affairs, for example. Why not me? I’m doing well at a “Top 25 University” and recently got done with a unique experience at another “Top 25 University”, studying international relations at both, I’m hot shit. Well, not quite. I don’t get any of them.
Mistake and lesson 1: Evaluate yourself honestly, and ask both your peers and those older than you what they did in your position. Don’t try to go it alone.
Spring 2015, Senior year of college at Wake Forest.
My adolescence was more or less defined by my parent’s insistence on taking school and extra-curriculars seriously so that I could get into a good college. This was the story sold to millions of boomers and their children alike. “Get into a good school, get good grades, you’ll be fine for the rest of life. There will be no shortage of opportunities for you, you may even get to choose what suits you best. It’ll be great!”
I didn’t need a lot of convincing, I liked school for the most part and put plenty of effort into sports, music, and more. I did the rest, too. I got into the best school I applied to, and I did well. Major in Political Science, Minor in Philosophy, 3.3 GPA. Fraternity involvement, political activism, study abroad, no disciplinary issues. So… where are those opportunities everyone talked about? My studies weren’t exactly the best suited to most professions, but it was surely enough… right?
Well, maybe not. As time went on, and I didn’t have a post-grad plan, I became more like an ostrich with its head in the sand. Part of me didn’t want to face the harsh reality of my idyllic little story being false. “Actually, no. You put in a lot of work but it’s not worth much, you’re probably going to have to start over and take a job that has little to nothing to do with your studies.” I scoured the school’s job board, went to the job fairs, nothing looked like a fit.
Panicking as we got closer to graduation and every, every single person asking you what your plans are, I did my first of many reactive moves. My dad was close with our local congressman who had recently been elected to office in DC. There was an internship for me there if I wanted it. He was a Republican, I definitely wasn’t. But oh well, it’s a foot in the door on the Hill. A lot of people find work on and off of it after some time there.
So, I took that option, found an apartment with a fraternity buddy, and off I went into the “real world”.
Mistake and lesson 2: Get real about the early career prospects for liberal arts students, understand that less than 30% of students work in their major field and you could be no exception.
Mistake and lesson 3: It helps to have a target and confidence, nobody wants to hear “I’m not sure what I want to do or what I am good at” even if it is very true. They can’t help you with that.
Fall 2015, Washington DC
Interning on Capitol Hill is cool. It feels important. The buildings are full of history, you walk past important politicians often, national issues impacting millions of people are always at the forefront. It’s neat. For interns, it’s definitely a tough gig as you’re mostly answering correspondence from angry constituents. Sometimes you get to attend hearings and happy hours where lobbyists kiss up to politicians for everything from agricultural transportation issues to arms manufacturers.
I’m operating a little incognito. Working for a Republican, and applying to entry-level roles at every Democrats office I can find. I send application after application. I don’t hear back from most.
Once, I finally got a response for a role in a Florida Congresswoman’s office. Awesome! When I got there, there were about 30 other kids there to interview at the same time, and they interviewed us at the same time! They went around in a circle and asked us to respond to short questions they had. I didn’t get invited back.
After 6 months, I’d had enough lying to myself and others about the work I wanted to do and was passionate about. (You can only take so many phone calls from angry Fox News watchers telling you that Congress should let border patrol shoot immigrants on sight.) I decided to leave that internship and go job-hunting full time. Surely with that freedom, I could find something in town. You know where this is going. I sent dozens of applications for all kinds of entry-level roles. Heard back from a few, interviewed, no dice.
At this point, I’m pretty demoralized. All of my friends from school in the city have some great first gigs. They go out on the town, they’re developing professional cred, I’m stuck in the mud, spinning my wheels. That little story I had been sold all my life is looking real bad at this point.
Mistake and lesson 4: Applying and interviewing is a very challenging game. Not only do you have to play it right, you have to bend the rules to get noticed and make it further into the process. I learned that the hard way.
Mistake and lesson 5: Your first job doesn’t have to be the job, it’s okay to take something you hadn’t thought of before as long as there is enough structure to support you through it.
Pittsburgh Summer 2016
Dad’s network to the rescue again. After a lot of huffing and puffing and no headway, I need some professional experience and to start learning what my strengths and interests might be outside of politics. A friend of his runs an investment firm in Pittsburgh that has a need for some young people to do work researching investments and helping build portfolio companies. Cool enough. I know nothing of Pittsburgh or of private equity, but it’s an opportunity to get going and show my worth!
Well, lots of ad hoc tasks later, it isn’t living up to its initial promise. At one point I was doing endless data entry for a manufacturing company still using Windows 98 for their operating system. Not exactly the professional skill I was hoping to develop, and that’s just one example.
Additionally, that firm was lacking any kind of structure or culture to make it a good place to grow a career. Learning opportunities? A system for goal-setting and rewards? Transparency into decision-making and processes? Roles to move into? None of it. I keep at it, though. I don’t have a choice.
Mistake and lesson 6: New grads need a huge spoon of humility. Nobody cares about your thesis and obscure books you read. At this point, you need to just prove you have a good attitude and can reliably complete increasingly difficult tasks.
Pittsburgh Spring 2017
Eventually, a worthwhile opportunity shows up. One of the new portfolio companies is a startup called UpContent that has a new search tool for marketers. My instructions are simple, show up and help out with whatever they need. Can do!
The team is small, only 5 of us at this point. Scott is the boss and he asks me to help respond to customers who are new to the platform and are having some trouble configuring their account. We’ll call it Customer Success.
Soon, 3 days/week there turns into 5. Then after a few months, I’m a full-time employee with UpContent instead of the investment firm. The company is small but growing. The work is repetitive, but over time I get to have more input on the ship we’re building, and where to sail it.
This is my first taste of a job where I’m respected for my input and can have ownership over how I execute the role. It’s stressful at times, as we’re scrambling towards profitability and we make plenty of mistakes, but my co-workers are awesome and we enjoy spending time together in a small room. Happy.
Soon, that window to become profitable closes and we’re running out of cash. As a nice-to-have employee, I’m out of a job. That sucks but it’s an opportunity to take the experience and skills I gained and get back to business as planned.
I wasn’t done with DC, I had something to prove. Armed with more experience, I set about applying to jobs in DC. Well, that confidence was short-lived. I’d forgotten how much of an insider culture there was there, and while I did have work experience now, it wasn’t the most relevant experience and I didn’t live in the area. I even went down there for a week to network with folks hoping to find some opportunities. Not much gave.
After a few months, I was feeling desperate again. “Well, I have some accomplishments with Customer Success now, maybe I can find something there…”
Mistake and lesson 7: You gotta be on your toes and always be looking for your next job. Don’t be complacent with your situation, you never know when it might get worse.
Boulder Fall 2018
After sending out dozens of more applications again, there was only one where I got past the phone screen, Customer Success for Techstars. At the time, the job description was only of passing interest to me, but the company and mission were great! It was a B-Corp, so they cared about people and the planet. They had offices and impact all over the world, I would have the opportunity to meet and work with all kinds of folks. They were large, successful, and growing. This was it, my opportunity to get back on track with my career! I could kick ass and move up here. I took each interview incredibly seriously and nailed each one on my way to the role. I was excited and finally feeling good about myself.
I packed all my shit up and drove back-to-back 12hr days from Pittsburgh to Boulder. (Kansas is as empty as they say, except for a huge windmill complex and air-force base)
I’m not sure if I ever had the right approach and attitude to the role. It was far more operations focussed, where I wanted it to be more relationships and strategy focussed. I tried to make it more like that by suggesting changes and prioritizing different parts of my work.
Techstars in a lot of ways is a great place to work. So many people with impressive and interesting backgrounds, all focussed on creating entrepreneurial opportunity for people around the world. Good perks and benefits, good culture of learning, and challenge. I got to work on the impact side, too, essentially working on a non-profit project for a for-profit company.
This where everyone tells you to stop, don’t bad-mouth your prior employers, it doesn’t do you any favors. This is where I feel like I have to stand up for myself, though.
I was never set up for success in that role. After a couple of months, the person that was training me and whose responsibilities I was taking was fired and not replaced for 8 months. The task I was hired for, implementing a CS program on top of a new CRM tool they were spinning up, never happened. A year later, I was still duct-taping solutions on the old platform. There were numerous legacy issues from the past owners of the programs. We were also missing the “customers”. We had volunteers who I was charged with making sure to follow our guidelines and have successful events. Except, they didn’t know what to do because our docs were out of date and lived on different URLs. There was no incentive structure. My success was mostly determined by my ability to motivate people to do ~100 hours of free labor for a company that boasted it’s portfolio’s $80b market-cap on its homepage. I had the largest, most active region (US/Canada) and the least support. Every suggestion for a process improvement was added to an endless pile of “we’ll get to it when we figure our shit out”.
We were a non-profit masquerading as a for-profit, in a services company masquerading as a tech company. All of the “figure it out” of a startup, none of the agility or fun. Disfunction abounded.
It became a perfect storm of frustration. I would bring up issues with our platform and processes, suggest changes, get ignored, and then get asked why there were issues with people using our platform. I was bored 80% of the time answering the same questions for everyone since they couldn’t be found online.
They say when you’re a young employee, your only real job is to make your manager look good. Well, I was making mine look bad because I would bring up my frustrations in team meetings about our inability to replace duct tape with lasting changes. I genuinely wanted to help build and steer that ship, instead, I was plugging leaks with my thumbs asking for help and getting none. When I would complain, the answer was “Work’s hard, what do you expect?”
That frustration bled into my attitude and performance and I was fired.
Mistake and lesson 8: Be wary of taking jobs for the sake of taking a job, it can turn out worse than you think in the long run. Be intentional with your career steps.
Mistake and lesson 9: Be more empathetic with your coworkers. When you complain about something, think about who’s work or ideas you’re complaining about. Always assume good intent.
Boulder Winter 2019/20
Well, there went my plan to get things back on track. Instead of building upon this role, staying at the company for years while I grew my skill base and network, I didn’t even make it a full year.
It was embarrassing and shameful.
I don’t think people understand the pain associated with being abruptly fired like that. With other social institutions fading in modern life, work represents a lot of emotional fulfillment for most of us. It’s social, our coworkers become friends and confidants. It’s actualizing, you feel connected to something bigger and can work on yourself at the same time. It’s sustenance, the pay allows you to pursue other goals in life. So when you lose all of that without much warning, it sucks. Really, really sucks.
My initial reaction was to be mature about it, own it. Don’t blame other people, don’t make excuses, face this like an adult, and accept the consequences. It was made worse when I reached out to various people in the company to either thank them or ask for their feedback/advice. I got 2 helpful responses. A lot of no-responses or trite ones. These were people who I had built relationships with, friends outside of work, or so I thought. I felt excommunicated and worthless again.
So, my emotional response went from stoic to angry with others and angry with myself. I let it happen again, I wasn’t proactive or professional enough to make things last. Here comes another setback, another gap in the resume, another long demoralizing job hunt. I wanted so badly to move on from my painful experiences job hunting, but here I was again. Plus, they didn’t get it. I complained because I cared, and wanted the best for my clients.
I spent the rest of October beating myself up and telling myself it was okay to take a few weeks to treat myself to time off to offset the bad moods. I played a lot of Playstation and went on a lot of hikes.
The holiday season came and went as I researched my next step.
This time I was determined to be proactive and intentional about things. I’m not applying to Customer Success roles, that was a role I was asked to do once and did because I could, not because I liked it. I’m going to find something that I want to pour more energy into. I have to break this negative feedback loop that I find myself in.
One of the more painful things about my professional failures is that it hasn’t been for lack of trying. I know that work is where you will spend most of your time and energy, I know it has the potential to make you feel miserable or make you feel energized. I wanted to get that decision right. I took career classes in college. I read multiple career books and lots of blog posts. I worked with career coaches.
I’ve had almost every advantage I could have in life, too. Great supportive parents (with connections), good education, no health issues. I’m an affluent white guy in America, how much easier do I want it? To be clear, I don’t want you to feel bad for me — the kid born on third base but got thrown out because he forgot to run home.
The effort, the fact that I know I should do better, seeing my peers accelerate in their careers, it all makes me feel worse about it. I know I shouldn’t compare myself to others, it’s unproductive but I can’t help it. It’s very human, after all.
One piece of advice you come across, again and again, is that you have find something you like enough to suffer for. Find that thing where the grind is acceptable because getting great at any skill or profession involves some amount of repetitive and difficult tasks. It’s the ability to make the work required a habit that determines success.
I’m an indecisive person, and I am afraid to commit to things that I am uncertain about. There were some cool-sounding paths, but they required commitment levels that I wasn’t ready for. (Masters programs, for example)
So, with the help of a local career coach, I settled on targeting jobs as a “Product Owner”. It appealed to my sense of ownership, leadership, creativity, teamwork and with a few courses I could add on to my prior tech experience to make myself an attractive candidate. I got scrum certified, I took online classes on product design and product analytics. I grinded. Sweet, I’m ready for a change! I spent February and March getting trained up and started applying. For the first time in a long time, I was optimistic about my career outlook.
You know the story by now, don’t you? Dozens of applications later and not a single response. Why did I think it would be different?
The job search process chews you up and spits you out again and again. I spent the first 22 years of my life feeling good about myself. Sure, there were times where I felt like I wasn’t adequate or capable (mostly in math class) but for the most part, felt like I was on a good trajectory for my life. The last 5 have been a roller coaster of ups and downs, but mostly downs. I don’t feel like I have much to show for it, I’m not proud of a lot of it.
You feel worthless. If no-one thinks you’re worth a salary to do a job for them, then you are worthless.
Individuals will tell you not to attach your self-worth to it, but society tells a very different story.
The stress of job hunting becomes all-encompassing. You doubt yourself in all kinds of ways. You doubt your abilities, your approach, and your thoughts (do I really want to pursue these roles?). Every passing week adds more pressure as you lose money, and the dreaded “resume gap” gets larger. You don’t want to be social because your fear the awkward “what do you do?”, or “ any luck?” conversations. You put off buying things and experiences, you put off dating, you put off all kinds of plans. Your life is at once busy and stagnant. You “work” but you don’t contribute. It’s not a fun place to be.
American culture is full of bromides about the importance of failing to learn, and getting up again. About giving and taking second chances, about seeing people for more than an 8.5"x11" sheet of paper that is their resume. I’m here to embody all of that.
When push comes to shove, though? Companies want to be confident that the hire they make will have good returns, and the hiring manager doesn’t want egg on their face. People typically only make two kinds of bets, safe ones, and exciting ones. Despite my best efforts, I don’t know if I’ve ever been seen as either.
All I can say now is that I’m ready, so very ready. I’m ready to put the sweat in to correct for all of these past mistakes that I have made. I want to make up for the lost time. I want to grind for something I care about, I want to get satisfaction out of my work.
Every potential employer will ask me, “Why are you looking for work and what have you been up to for the last 8 months?” and I will do my best to repackage that story as a positive so that they’re not scared away by the one negative that I have to show during the process.
But here is the real story. I’ve been lazy and scattered in my job search in the past. At work, I’ve often been stubborn and eager to be taken more seriously than maybe I deserved. I’ve paid for these mistakes by taking roles for the sake of it, and as a result, never finding much success or traction.
Despite all of that, I still believe in myself. I believe in my intelligence, and my personality. I pick things up quickly and make friends wherever I go. I’m never short of ideas. I want to apply myself in the right situation, I just need someone to give me the chance despite all of these mistakes I’ve made.
