Why Outliers Who Overcome Make the Best Entrepreneurs

AKA…my origin story. Do you ever think about the external and internal struggles that led you to where you are today? On this wild entrepreneurial path we go down, there’s always a “hero’s journey” somewhere in the story about how you hit a wall and then found a way to overcome it, transforming yourself and your business in the process. Here’s mine.

Contemplating all the trolls I’ve battled in my career, under the Fremont Bridge, Seattle. 😉

I’ve been an outlier my whole life and I don’t mean that in a “feeling sorry for myself” kind of way. It’s more about always feeling that I was not a part of the mainstream, that I didn’t fit in, didn’t really want to fit in, and was definitely NOT like everyone else. There are many good things about being an outlier — you’re usually not overly swayed by societal norms and pressures. If anything, you RUN from them. You are a natural outside-the-box thinker and can see more than the surface value of people and things. You’re never afraid to try something different, take risks, and take the path least traveled.

But it comes with its own set of problems too. People don’t like people who don’t want to belong or go with the flow. It’s challenging…it produces a range of reactions, from “who does she think she is?” to “she’s weird” to “what’s wrong with doing what I’m/they/we’re doing, anyway?” It challenges peoples’ core beliefs about how things are, or how they should be. It’s not a cakewalk for the outliers either. It can be a struggle to get by in school, deal with authority figures, succeed in regular jobs, and maintain relationships. If you’re seen as rebellious, there are always going to be those around you who want to squash that rebel spirit and rein you back in.

All the people I respect now were once outsiders. From Girlboss Sophia Amoruso, who was seen as a loser who couldn’t hold onto even a low-level job to an empire-building badass who still felt uncomfortable with mainstream titles and events like CEO and “Fashion Week,” to Vin Clancy, whose story involves going from living on welfare to selling two companies and then making enough money to “retire” from his regular consulting business in just 4 years, by writing a sort of growth hacking bible for mavericks. Which he definitely also is (see below) — no wonder I resonate with this fancy unicorn.

Here’s Vin Clancy dispensing “free life advice.” 😏

So this is my story. I was an outsider introvert from the time I was a small child. I realized early on I was never going to be a popular kid in school because I was incredibly shy but also more attracted to the quiet smart ones and the artistic weirdos. I was constantly observing and filing away info, but from a distance. I didn’t realize till much later that I was doing what writers do. I told my parents at age 12 that I wouldn’t be going to church with them anymore because everyone there was a hypocrite. I did group things like Girl Scouts and summer camps and volunteer work, and that was because I enjoyed the social aspect as much as I wanted to look good on my college applications. But otherwise I stayed away from groups — I had a particular dislike for organized religion and team sports. Instead, I read new age spiritual books and did gymnastics and took dance classes.

I was told by some of my favorite English teachers in high school that I was an “iconoclast” and that I could influence people with my writing. I never forgot these two bits of feedback because they meant something to me, something major.

I was an Honors student and always made good grades (well, except in most math classes), but I still lacked a certain drive and ambition to achieve things that I saw in the fellow smart kids around me. I couldn’t apply myself to things unless I felt truly passionate about them, and even then, I was good at starting things (blogs, webzines) but not so great at seeing them through.

I also put a lot of pressure on myself to achieve great things and bust through barriers — I never felt like I was achieving enough, and that there were too many things holding me back. This feeling persists today, but I at least have a better handle on how to get there and more clarity around what exactly it is I’m MEANT to do in my career. I wouldn’t say I reached clarity around both things until recently.

After a year abroad in Spain as a foreign exchange student, I went to college and the only real direction I had, besides continuing to bust out of my self-constructed shell, was that I was going to pursue a career that was centered on writing. At first I thought Journalism, but in the two newspaper/magazine internships I had post-college, I discovered that I actually hated constant deadlines and hated critiquing other peoples’ creations (I was a music critic for awhile). I didn’t want to spend my time writing snarky takedowns of local bands or fangirl soliloquies about already established artists. I wanted to create too.

My first real post-college job was at one of those classic San Francisco Internet startups. The City was just entering the dot.com boom days and I had joined an early search directory dreaming of a booming IPO. I loved this job, not because it was challenging or all that interesting, but because I worked with 100+ other smart, artistic word people (Web editors) all between the ages of 24 and 32. I made so many friends there and we had a blast. I finally felt that I was a part of something cool. From having to put my own desk chair together in a small loft office, to getting my first manager role at age 26, to cashing out about $50K worth of stock options, only to spend it all and then ultimately get laid off…I went through the full dot.com boom and bust experience.

Yep, the TV show Silicon Valley got a lot of things right about early startup culture in SF — but swap the Lambo for hackey sack and the suburban home office for a trendy brick walled SOMA office and keggers.

I also experienced my first major disillusionment with higher-ups at a company and workplace corruption in general. The company had started in Australia and the whole exec team moved to SF — their concepts of sexual harassment and workplace appropriateness were very different and didn’t fly in the US. The majority of the editorial team also ended up with carpal tunnel syndrome and even had to get physical therapy (me included) because the work we did was so incredibly repetitive. Still, I stayed there for 5 years.

When I finally decided to go for a voluntary layoff, I didn’t expect the existential crisis it would throw me into. I was living in a dream Victorian flat a block from Dolores Park that I could barely afford on my dot.com editor’s salary, and when I couldn’t find a job right away, I REALLY started to struggle. It wasn’t unusual for me to sell my clothes so that I could buy food, because every bit of my severance pay, unemployment, and income I eked together from contract gigs went to rent and bills.

Eventually, I moved out and in with a friend in a much smaller and less impressive apartment. It felt like a big step back at the time, although we also were living in a desirable part of SF and had a nice flat. I continued to struggle to find a job…I even started walking dogs and dogsitting through a Craigslist ad I put up, which was actually decent money. You could even say this was my first bout of entrepreneurship. I could’ve turned that into a business, but it wasn’t what I wanted to do. I mean, I was a cat person, ok?! When I finally found another Web Editor gig, it was for less money than I’d been making before, plus I had a shitty commute to the South Bay.

That job experience would set off another pattern for me — I was totally bored and unchallenged so I completely disengaged from the job, worked only as much as I had to and spent the rest of my time chatting on online forums and writing my own stuff. I had one good friend there, a similarly snarky and subversive guy, and that coworker relationship was the only one I put any energy into. Later I would end up hiring him to work with me at a big job. I didn’t make the best of that situation, I just did what I needed to do to get by.

Just a typical Tuesday night in the mid-2000s.

Eventually, I left this job for another risky situation — I knew that I wanted to pursue community management jobs as a career (having gotten some of this experience at my dot.com job), and so I took several low-paying contract gigs while living in a cheap apartment with my boyfriend at the time. He was a karaoke host, and so my non-work life pretty much revolved around getting drunk several nights a week at his various karaoke gigs and getting into trouble and drama with the regulars…a very motley crüe of people: tech geeks, former theater nerds, people in cover bands, drama queens, chaos merchants, pick-up artists, ex-drug addicts, people with great careers but terrible relationship histories, etc. We were one big dysfunctional family and did a lot of fun and creative things, but ultimately it wasn’t the healthiest scenario. It was hedonism, pure and simple.

The turning point for me was when I got my first full-time community manager position — I joined an existing team in an entry-level role at a virtual world. I eventually became bored there too and didn’t feel I fit in with the über gaming nerds that made up most of the company, and was ironically then swooped up and recruited by a global consumer electronics and gaming brand to head up the community for their virtual world for gamers. It was just about to launch, and we were like a startup within this big brand — a brand new team of some of the best and brightest I had ever worked with.

My upward leap was intoxicating and lightning-fast. Suddenly, I was leading and building the entire US community team, flying to London my 2nd week of work, working with people so smart and accomplished that I worked overtime every day just to prove myself worthy and not let them down, giving high-level presentations to global teams of C-suite members, getting press training, you name it. My salary also increased by 60% and suddenly I was in a whole different world of possibility and opportunity.

Clowning with the work crew in London…yeah, ok, so there were *some* perks to being in the boys’ club.

I felt challenged every day and also struggled with “imposter syndrome” — I spent a lot of time doubting my own abilities even though I was getting lots of kudos and good performance reviews from my boss and knew I was pulling off good work against high odds: a glitchy product, a very hard-to-please community, and snarky and unforgiving gaming press. I was also the main target of much of the 12 million-member community’s frustration because I was on the frontlines as the head of the community team. When my identity was accidentally leaked by one of my problem employees, I got to experience what it was like to be harassed and stalked online by angry, cheeto-dusted, woman-hating teenagers living in their moms’ basements. Yeah, good times.

I also had a pretty major health crash during this time. At its best, the job was challenging, exciting, and prestigious. At its worst, it was toxic, demoralizing (hello, boys’ club culture), and incredibly stressful with daily fire drills. One of my coworkers developed shingles. I was having chronic fatigue, brain fog, insomnia, dizziness, and constant illnesses. I wouldn’t find out until I left the company that these were all symptoms of adrenal fatigue….an illness literally caused by stress. It’s something you can only “cure” through diet, supplements, and lifestyle changes so it’s been an ongoing journey of recovery ever since.

Several on the team, including my boss, also had major relationship upheavals. Things were falling apart. My boss changed drastically from the super-enthusiastic, driving leader to someone erratic, alternately manic or depressed, who pitted us against each other, took things out on us, and thought he could make up for the failure of the product by increasing the pressure on us. I’ll never forget the time he threatened me in his office…cold eyes boring into me, he said “I cannot fail.” Never mind that if he failed, we all failed. It was no longer a team and we were no longer in it together. I became increasingly disillusioned and depressed.

Three of us in senior management left the company within months of each other, others played politics to get into other positions or hired by third-party vendors, still others stayed and weathered the storm so they could keep climbing the corporate ladder. I went to HR about the many abusive tactics I was experiencing from my boss, and got nowhere. As I learned the hard way, corporate HR protects anyone director level or above, end of story. Cue my second major work disillusionment. Had I said nothing to HR, kept my head down, and continued to drive my health into the ground, I would have been “rewarded” with a high-level marketing position, higher salaries, and ever-climbing bonuses, as well as plummeting fulfillment levels. It’s still weird to me that this type of scenario is the “prize” we’re all driven to pursue…the proverbial brass ring at the top.

Chasing a work life on someone else’s terms can have an untold cost to your health, happiness, and relationships. And for what? To make a couple of old white dudes at the top (usually) rich while collecting the “crumbs” of a 401K plan and a salary that *might* increase by a few percentage points year over year, while trying not to die early from stress. No thanks.

That was my second and last corporate experience and I never really recovered from it. In the sense that, once I’d experienced the whole dog and pony show there was no going back to it. I couldn’t go into new jobs without being on high alert for abusive bosses, office politics, and toxic culture. After my gaming job, I got and quit 4 other jobs within the same year. It wasn’t unusual for me to get feedback from job interviews (and I went on a TON of them) that I was “too easygoing” and not excited enough.

This offended me at first because I thought..”since when is being easygoing a BAD thing?! It means I don’t panic for no reason and can solve problems without losing my shit. And it’s actually a great quality to have as a community manager.” But I knew the problem was bigger…I didn’t truly believe in the company or people I was meeting with, and therefore couldn’t fake enthusiasm for getting the job. In most cases, it was just a paycheck to me.

So I jumped from one job to another and even kept pursuing the gaming world, because I thought it was what I should do. After all, the industry was blowing up in San Francisco, and I had covetable experience. I had a couple more stints as a community manager in gaming, but got laid off from both only months after being hired due to company instability. I was also getting jobs as a social media manager and although it was a different skill set and I was very green, I soon realized it was easy to get freelance consulting gigs doing it because most companies didn’t care if you were in-office or not.

And so a consulting career was born — I got my first clients through staffing agencies or through friends, and those weren’t the highest paying. But these connections led to other connections, and I was soon getting most of my gigs through network referrals or from my LinkedIn profile. The power of networking was working for me, and I was accumulating a decent client list of successful startups as well as global brands like Levi’s and Microsoft Xbox. I became very comfortable with all the tools and tricks of my trade and was achieving results for my clients. I FINALLY was starting to feel like a success on my own terms.

Eventually, I took this and created a small consulting agency with my fiancé Doug and we called it Cipher Collective. We brought another social media/marketing person onboard immediately and started taking on bigger projects, such as creating a social media strategy for a sponsor at Dreamforce. Later on, we connected with a great graphic designer/Web guru and used him on many projects — our vision of a creative collective was happening!

Cipher Collective in one of its coolest iterations. 🙏

Naturally, the story doesn’t end there and our business journey has been ever-evolving. One issue we had is we tended to get the same type of gig over and over (mostly social media and content-based), and work with the same type of client: small to mid-size businesses who didn’t want (or weren’t able) to pay more than $3K on a monthly retainer.

In between all this, we had a child (born in early 2016), which also threw our lives into a whole new type of chaos. Even though Doug had gotten a sales job while I was pregnant to help give us a little more security than relying on client payouts, he hated the job and I only had part-time work myself. I realized I hadn’t left myself in the best position — I wouldn’t have maternity leave and thought, wrongly as it turned out, that I could just work straight through the newborn months. I even scheduled social media posts for a CEO I was working for from my hospital bed, the day after my son was born. Total madness and not sustainable. I actually ended up becoming quite ill and losing the gigs I had because I couldn’t keep up with the work and had stopped sleeping. Then we were really up against a wall, and when I recovered I went back to FT office jobs because we needed the secure paycheck. It wasn’t at all what I wanted, and I knew it wasn’t going to be sustainable in the long run.

With our business, we found that we were expending a lot of energy for not enough return and also weren’t great about marketing ourselves while we had work…we’d usually only pay attention to this when we were seeking new clients. A common dilemma with the self-employed. I started thinking a lot too about how I wanted to scale this, and how to do that in a way that matched my career vision: do I want to be a true full-stack digital marketer and work with clients who wanted the full gamut of services? Or do I want to put more time and energy into creating valuable content that I could sell and then create a passive income stream from? Do I want to design online courses, write books, be a speaker at industry conferences? Does all this add up to eventually becoming some sort of inspirational business/lifestyle coach?

The answer to all of this is both YES and TBD. I spent all of 2018 chasing shiny object syndrome and going down rabbit hole after rabbit hole of exploring different types of businesses I could create under the Internet Marketing umbrella. Spoiler alert: there are tons of them and each idea is backed by hundreds of “gurus” selling the secret to getting there. Some are legit, some are total scam artists. You can waste a lot of time and money listening to the wrong people.

Luckily, the people I invested with as mentors were legit and have helped me a lot both with tactics for growing my new business, but also with the big picture view of what my ultimate goal is for my business and who I want to serve. I also want to create a strategy that not only works but is aligned with my personal values. I don’t ever want to go back to working in a 9-to-5 job in a toxic corporate environment…I want to remain independent, self-employed, inspired, and create a legacy for my family.

Cipher’s business legacy today lies somewhere between The Matrix and Old MacDonald’s farm.

I believe this is all possible and although challenging, I intend to have a lot of fun getting there. If you want the same thing for yourself, there are endless ways to get there. I recommend finding a mentor or coach who you resonate with and trust and getting some one-on-one help (or least get it in a group setting). And feel free to message me or drop me a comment if you’d like more advice on how to find a mentor, or anything else related to being an entrepreneur. It can be a lonely game, but it doesn’t have to be.

One of the best things I’ve done so far in 2019 was to join the One Funnel Away challenge so that I could get a funnel launched for my new business offering (launch copywriting services). If you’re on the fence at all about what to do and want daily ACTION prompts through coaching videos, homework, and worksheets, this is a highly valuable and motivating 30-day challenge. I’m doing it right now, and can't recommend it highly enough. Join me for the next one!

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +436,678 people.

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