You Can Quit Entrepreneurship...The Dirty Little Secret I Kept to Myself

[And how I re-entered the workforce after 5 years of hustle and grind as an entrepreneur]

"I quit my job!" is often celebrated.

It signifies freedom from the 9 to 5 shackles. Which to be honest had been a sentiment I shared when I ended my full-time job after 10 years in the social service sector.

Whispers, "I quit entrepreneurship"...now that's a statement that is burdened with shame of failing to make self-employment work. However, for me, it signified the freedom to manage my mental health.

At the time though —quitting entrepreneurship —was the dirty little secret I kept to myself.

Anybody who has ever worked for themselves knows —your brain nags you about everything you could be doing in your business instead. Even at social events, you're thinking about sending out a contract or how you're going to respond to an email.

That being said, let me start from the beginning, where my business launched and what led me to quit entrepreneurship.

Have you ever felt like, you're supposed to do something with your life but yet to figure out what? I felt like this —the majority of my twenties.

Following the path set out by my Caribbean parents: Go to college, get a good job with benefits then retire 35 years later. Well, what if you complete the mission in less time and still feel lost?! I did what was laid out for me and still felt a void.

That sent me on a tailspin of seeking and searching for more.

When I was in a permanent full-time job, I took a contract Communications role (something I didn't go to college for). This well-intended plan was to force me into starting a business 1 year later. The unexplainable feeling I had earlier that made me feel empty inside morphed into: "Start a business, but what?"

Since I went to college for social work with a minor in Psychology, it made perfect sense to become a life coach, right? Sure. That's what I did for the first quarter of my leap out of the workforce. I didn't make any money in my coaching business for 6 months.

No steady income...while in school...and not making a single dime from this "business" I decided to start —just call me loco…my co-workers did!

In my zig —when I should have zagged, I noticed not only myself but other coaches struggled to express what they did in their business. I also spent the majority of my time on marketing and messaging than actually coaching anybody, anyway. So I pivoted.

That's when my true journey of entrepreneurship began in copywriting.

At the time, I didn't even know what copywriting was. What I did know is I could write —mainly poetry but writing nonetheless. Never once did I imagine I could trade writing for money. This led me to write my first online publication without securing one red cent but I was being featured in outlets like the Huffington Post, so that added to my online credibility I told myself.

However, when I eventually found out how to get paid for said writing, I also learned I was in an industry that is known for prolonging payments to writers. How can one live off compensation uncertainty when bills show-up like clockwork?! It was an unsustainable endeavour for me, so I pivoted again.

That's when I stumbled onto a woman online making a significant amount of coin by writing for entrepreneurs. Remember that zig when I should have zagged?

Coaching should have led me down this route instead but when you come from a background of not seeing what is possible —possibilities can look out of focus.

When my vision did eventually align, I began my own copywriting business, for real this time. Still not 100% knowing what area of focus or direction I wanted to go (i.e. B2B or B2C) but I dived in with all ten toes because I could effortlessly combine my gift to identify a message unique to a business and make it marketable. I didn't know it was a gift then —I just knew others couldn't do it, so I ran with it. Which eventually landed me my first contract with a Fortune 500 company and running a content marketing workshop at the Microsoft Store.

Yet, entrepreneurship is hard.

This is what I've learned running a business full-time for the last 5 years.

• The highs are high: the amount of money you can make in one month compared to in a year, securing opportunities you're not trained for but are named for, and the incredible people you have access to.

• On the flip side: the lows are low when you don't fully understand the ebbs and flows of your business and then go broke for 4 months. And TAXES! Ugh, my Achilles heel and arch-nemesis.

I did finally find my rhythm but not until I returned back to a 9-5 and realized established businesses struggle too! This newfound perspective, yo-yo'd me back into my copywriting business full-time only to realize AGAIN, entrepreneurship —it's still hard.

There is a steep learning curve when you work for yourself.

You need to know when it's the right time to hire a team, lean on experts in your area of weakness and properly plan for the high and low periods in self-employment. Which takes a full plate of guts, instinct, and a side of discipline when sometimes all you want to do is work and collect a paycheque.

So here I am, back in full-time employment after applying to 108 communication & marketing jobs and showing up to 13 interviews within the course of a year. See also; putting my lessons into practice, continuing to work on my craft and digging deeper into my field of expertise.

There were a few things I did to re-enter the workforce, after 5 years of F/T self-employment and being asked the eye-twitching interview question multiple times, "Why do you want to return to a job after working for yourself?"

1 ) I Tracked Every Single Job I Applied And Interviewed At

This allowed me to properly follow-up with recruiters and hiring managers when I sent “Thank You” emails after the interview or after rejection and how often they put out positions to gauge culture fit (also to simply remember the employer. Sometimes jobs contact you 2-8 weeks later).

2) I Upgraded My Skills

I am an avid learner. So that meant, I increased my skills from writing classes to a marketing and sales course to certify myself as an expert. I found out from the roles I wanted —what they wanted from an ideal candidate.

3) I Sought Advice From Friends And Associates Who Worked in the Recruitment Industry (And Also Hiring Networking Events)

This did two things: gave me insider insight (i.e. The Star Interview method) and put myself on their radar to send jobs that were a match for my skills. Cha-ching!

4) I Wrote Scripts

Applying to jobs via ATS, sending follow-up “Thank You” emails (snail mail and e-mail), follow-up rejection script for collecting feedback, a script to do cold outreach to hiring managers on LinkedIn and even for the popular opener interview question "So, tell me about yourself?" Don't wing this question, this is an opportunity to set the tone for the entire interview. Learn how to articulate your value as it relates to the role via storytelling.

5) I Submitted a Customized Cover Letter, Resume and Portfolio for Every Position I Applied

Yup. Don't overlook this step. It's time-consuming —yes, but most people like to hop over it and that's how you stand out. I've heard back from hiring managers that because I took the extra effort to do this they were curious to learn more about me (3 out of 12 job rejections turned into contract roles for my business) 🙏🏾.

6) I Got My Mind Right

Uh...this was the hardest part. I had to do a lot of pep talk to remind myself I wasn't a failure for not making it as a full-time entrepreneur. I had to put other things as a priority, investing in myself (and that meant time, grace and the ability to take a break). My business didn't allow room for that, I was always hustling...and so, being back in a job provides the balance that I require to thrive even further.

*I am sure there are a few more tidbits I could share but maybe in another blog post, we’re creeping up to 1500 words now.

This once upon a time feeling of shame "failing at being an entrepreneur" and returning to a job, has now transformed into me (finally and) fully understanding there is no failure —only what works for your growth.

And working full-time while running my business on the side is most ideal for my growth (at this moment). Considering what entrepreneurship has beaten me over the head with: nothing is certain only how creative you can be with possibilities.

Are you returning back to a job after entrepreneuring? What’s your story?…

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