The Unemployable Entrepreneur
I stopped counting after 126.
Hours spent hunched over my keyboard in my dimly light apartment crafting cover letters. Searching for the perfect combination of words to capture the attention of the illusive hiring manager.
You can only take so much rejection.
So I stopped counting after pressing send on 126 attempts to get noticed.
Less than 10 replies, fewer “screening calls” booked, and ultimately zero offers made.
Feeling like an old-school door-to-door salesperson, is this what it has come down to? Is it just a numbers game? Keep knocking on doors until someone buys what I’m selling.
Leaving the answer to the dreaded question “Why do you want to work for us?”...
…With the unfortunate reality of the answer “Because you’re the only one that responded…”
That’s not what they want to hear, fyi.
Stupid fucking question, right?
Do they really think they are the only company I applied to?
I digress.
It’s interesting how being an entrepreneur can make you unemployable.
Or, at least that’s how it felt for me.
You see,
I’d been an entrepreneur for over 10 years.
And as a young freelance entrepreneur, you do what it takes to pay the bills.
Anything my clients needed I would figure out how to do.
I was designing ads to be printed in newspapers, building and designing websites, fixing code in programming languages I didn’t know, designing logos, building spreadsheets, setting up email accounts, and doing work for 4-5 agencies in my city - whatever they needed and were willing to pay for.
It didn’t matter if I could do it or not, had experience or not, the answer was “Yes”.
As an entrepreneur, our core skill set is often figuring shit out.
On a resume, this is called resourcefulness.
I even built an iPhone and iPad app for a company.
I had no idea how to do this. I had never built an app. I didn’t even have an iPhone, iPad, or even a Mac. But I found someone to outsource the work to. When it was complete I had to search on Google for a tutorial on how to even test the app before sending it to the client.
(The app worked and the client was very happy)
There I was, with over a decade of experience under my belt, unable to get a call back from prospective employers.
I was at a point in my professional career where I sought a change.
That change was to go from being a lone wolf always on the hunt to working with a larger organization.
I never could figure out why it was so hard.
Was it a lack of visible experience on the resume, or the fact I was an entrepreneur that stopped the doors from ever being opened…
My confidence is 10/10 to accomplish any task put in front of me.
But when the requirement says:
“3 Years Experience With Google Analytics”
Or,
“6 Years Experience Working With SaaS Companies”
I struggled to check the box.
Had I used Google Analytics? Yes. Had I worked with SaaS companies, Yes.
But, as an entrepreneur, I didn’t ONLY work with them for all those years. So my experience was spotty and sporadic at best and a lie at worst.
To this day, I have been an entrepreneur my entire life.
18 (or 20, I’ve lost count) years as an entrepreneur and I still feel unemployable.
The system is kind of rigged against us.
People say they want “intrapreneurs”, self-led individuals, and A-Players. Nothing says that more than an entrepreneur.
Hiring practices (in my experience) show something much different.
If an entrepreneur is not self-led, doesn’t get the job done, and doesn’t leave clients happy? They don’t eat.
But, seeing this experience on a resume doesn’t get noticed.
What’s noticed is highly specialized experience for extended periods of time.
Take your pick, Ads, CRO, Copywriting, SEO, Etc. Even entry-level positions require 2+ years of dedicated experience with these.
I’ve done them all, at varying points in my career, but I didn’t spend the last 2-5 years doing only one of them as a specialist.
My experience is extremely broad from the diverse set of things I have done throughout my career - I’m a generalist.
This also makes me think switching careers would be extremely difficult.
A few years ago I thought it would be cool to become a writer.
So I poked around some job postings to see what was available. Everything required a min. of 2+ years working as a copywriter.
But, even more, they were all specific. 2+ years writing for a publication. Or, 2+ years writing blog posts. 2+ years writing social media posts for SaaS companies.
So how does someone get noticed? Or even start?
Here’s what I’ve come to realize are the three things we can use to get noticed regardless of what our resumes say.
Because the reality is, I am not going to spend 4 years working for min. wage as a writer (or anything) so I can work up to being “eligible” for one of these jobs.
Networking.
Become a thought leader.
Partner with someone.
Networking
We still and I predict will always live in a world of “who you know, not what you know.” Nothing is easier than getting noticed because of someone you know. Networking gives you this leverage. The more people you know, network with, and build relationships with, will always put you in a stronger position than anyone just dropping in a resume with a ChatGPT written cover letter.
Become a thought leader
Think of this like “inbound marketing”. If you’re a thought leader in your space you increase your chances of getting noticed. Not unlike marketing your business, you will also increase your chances of being noticed by recruiters, prospective employers, or when the hiring manager checks your social media profiles.
Partner with someone
Partnering with someone can be a bridge between entrepreneurialism and getting “hired”. Let’s say you’re a bit burnt out from being a lone wolf and always on the hunt, but you obtain a diverse skill set, you can partner with someone who compliments your skill set and needs your set of skills. Together, you can still maintain your independence, while getting the support from someone similar to the team or managers you’d have at a company.
For all the entrepreneurs, freelancers, coaches, creators, innovators, and builders out there…
I know this game is not easy. But I think we can all agree, deep down we love it.
It’s who we are. It’s in our blood.
-Landon.
PS: I’m still an entrepreneur.
PPS: Here are a couple of letters you may enjoy:
This Is Not What I Thought My Life Would Look Like At 35
https://landonpoburan.substack.com/p/this-is-not-what-i-thought-my-life
How To Publish 5 (Or More) Pieces Of Content Every Day While Working Full-Time
https://landonpoburan.substack.com/p/how-to-publish-5-or-more-pieces-of