I’m About to Risk Everything to Go All-in on Pursuing My Dream, and I Feel… Fine?

Greg%2Blooks%2Bat%2Bsunset.jpg

Friends and well-wishers… my life is about to take a drastic, albeit thoroughly planned, turn into the unknown.

At 10:00am on July 4, 2004, a nervous, pimple-faced, rail-thin, 16-year-old me stepped foot into the Americana Resort & Spa’s brand new indoor waterpark in Niagara Falls, Ontario, equipped my whistle, sunglasses, and flip-flops to start my first day on the job as a lifeguard.

And ever since that moment… I’ve had a job.

Sure, there was that 8 week stretch after my 5th year or university where I “took a little break”, and of course my infamous 5-month unemployment spell when I was trying to get a U.S. work visa after grad school, but these were always short-term, temporary gaps in employment.

As of 3:30pm on Friday, July 31, 2020, I’m leaving my job for real… on purpose… forever.


The Decision to Leave

If you’ve been following for a while, you may remember that I had a pretty rough October of 2019. I documented that shit-show in this post entitled How the Hardest Month of My Life Made Me Believe in Myself and Follow My Dreams.

For those who don’t have time to read the whole story, a quick recap… I attended multiple funerals, my best friend moved across the ocean, and I narrowly missed out on a promotion I had been dreaming of for over a year.

That missed opportunity was the push I needed.

To be honest, I had been thinking about departing for about 2 years prior, but I was kind of addicted to the comfort of having a routine and working with people I was familiar with so I stayed.

Thankfully, after that major let down (the no-promotion), a few of my bosses and co-workers had conspired to help me out, and the moment I was denied that job, I was offered a “consolation” job which was a 6-month contract in another department.

It was by no means my dream job (although it was working for my dream boss), but it was my opening… take this job… 6 months… then I’m out! Go full-time on my resume-writing / interview coaching business.


But What About Money? Please, Don’t Starve to Death

As I detailed in my blog post, I Quit! Why, When, and How I’m Leaving My Steady Job to Run My Business Full-Time, my first reaction to not getting that promotion was to hit the spreadsheets… hard.

At 5:00am, the morning after I got that bad news, I generated 8 different financial models for different timelines that outlined when I could safely afford to leave my job according to my personal/business expenses and cash-flow projections for my business.

As you may know, I’ve been saving just about every penny from my side-hustle since the day it started, and as I explained in my post, How I live in a Luxury Downtown Highrise Condo on a $65,000 Salary while Putting Away $20,000+ Per Year in Savings/Investments, I’ve been aggressively contributing to my Tax-Free Savings Account, my pension, and what I like to call my “Rainy Day Fund” for 3 years (5+ years on the pension)… pretty much since the moment I finally paid off those pesky student loans.

In addition to all my savings, during this 6-month job I was paid a fair amount more than my last job… so I’ve been dumping 25% of my paycheck directly into my Rainy Day Fund for the past 6 months on top of the years of saving before hand.

Aside from my home and my vacations… I’m not much of a money spender. In my mind, I’ve spent these past few years imagining that I’m buying time as opposed to things. The more money I saved, the longer I could afford to run my business full-time without earning enough to cover my monthly expenses.

At this point, according to my most conservative cash-flow predictions (which would have me making a fair amount less than I’ve made the past few months), I can support myself for about 18-months on my Rainy Day Fund alone before I need to start “breaking-even” or dipping into my long-term savings.

Now… do I plan on taking 18-months to break even? Hell no!

In May, I was only $197 short of “breaking even” to cover my monthly expenses and in June, I was only $329 short. That gave me a lot of hope.

Bottom line… I won’t be starving to death… but thank you for caring.


My Biggest Fear and How I’m Combating It

The biggest perceived obstacle for me when leaving the known world of having a full-time job is definitely the loneliness. I am a self-proclaimed hyper-extrovert… not that I’m hyper like you would call a child… okay, sometimes I am… what I mean is that I’m just extremely extroverted and I really really like to be around people.

Working on my own full-time… it won’t be conducive to social interaction. I fear the loneliness will sap my energy and that’s where I’ll flame out.

However, I am not one to ignore a challenge… I’ve got a plan… actually… I’ve got several plans.

Please allow me to explain.


1. COVID-19 Means Ariana Works from Home

I’ve got the love of my life within literal arms reach (our den is very small and we’ve crammed two desks in here), so for the first 5-or-more months (who freakin’ knows…), I literally will not be alone.

Is it annoying / distracting being that close to someone all day long every day? Duh! But it’s worth it because she’s cute / hilarious / excellent / reading this blog post.


2. I’ve Joined 2 Entrepreneurial Communities

As if by magic, I received two applications for brand new online entrepreneurial communities hosted by my 2 favourite entrepreneurs / heroes, Pat Flynn and Chris Guillebeau within 2 days of each other back at the end of June.

I applied to both, was accepted to both, and joined both groups. Now, I’ve got all these people in my network who are at various stages of doing the same sort of online business type stuff that I’m doing. We’ve had Zoom meetings, shared messages, ideas, feedback, encouragement and all that great stuff.

Once we’re allowed, I’m hoping to find and/or create another Mastermind group that meets physically… but I’ll cross that bridge when it is safe.


3. Lunch Dates… Lunch Dates… Lunch Dates

Luckily, I’ve got a solid list of friends who work downtown near my condo. When the day comes that everyone is back at their offices, I’ll have a wide roster of candidates with whom to break bread over their designated lunch hours. I’m also looking forward to subwaying back up to York U to visit with my old co-workers on the regular... I love those peeps.


4. Co-Working

I’ve got some really great friends who are with a) self-employed, or b) work remotely, who I’m planning to get together with on a recurring basis to quietly pursue our independent goals in the presence of other living beings. I’m not really thinking about paying for an office in one of those nice co-working spaces yet (gotta keep the business lean at the moment), but having this arrangement with friends to break up the alone days will be nice :)

I think I’m going to be a-okay for this one as well :)


What am I Most Excited About?

God… there are a LOT of things!

I genuinely don’t know where to start. I’ve got butterflies in my stomach thinking about this (like the kind you get when you see your crush walk into a room in high school).

Let me just try a quick list of things I’m excited about for you:

  1. No more boss: The ironic part is… I’ve had a line up of probably the greatest bosses the world has ever seen. Level-headed, caring, people-first professionals who I dearly love. But still… having no one in the world to tell me what to do (except Ariana) is all I’ve ever wanted.

  2. Performance-based income: I always felt frustrated that no matter how well or poorly I performed at work, my paycheck was always the same. I know a lot of people like that stability (for good reason), but it’s never felt right for me. I believe in myself to thrive and I want my income tied to that.

  3. Exponential income growth: At York, I would get like a 1.5% income bump every year. When I took on the temporary contract, I got a 15% raise. In contrast, running a business, I can grow my income a lot faster. My first year, I earned about $8,000, my second year, $15,000, this year, I’ve already surpassed last year’s earnings.

  4. Location freedom: This is mostly a post-covid thing because I’m fairly confined at the moment, but long-term, I’ll be able to work from anywhere. If I want to spend time with my parents, take an extended trip, or even just hop on the ferry and work from the island for a day… I can.

  5. Having 100% control over my own vision: I have a LOT of ideas for new projects, new income streams (I’m going to announce a BIG ONE in the next couple weeks), new marketing tactics. And now I will have the time, energy, and freedom to take those in whatever direction I want.

  6. No safety net… and complete commitment: I can’t count the number of times I’ve delayed writing blog post or recording a video course because I knew my York U paycheck was coming in on the 25th of the month. Without that, the fire under my butt is lit, and I am READY. TO. ROCK!!!

There are dozens more things I’m excited for, but you get the gist ;)


Do I feel any sadness, regret, nostalgia leaving York after 12 years?

I left York once before to go to grad school in Florida. That was really, really hard. I cried… bawled actually… like a pulsing, weeping mess. It was my whole life for 6 years and I left. 2.5 years later, I was back… and I stayed for 6 more years.

Now I’m leaving again.

I feel a lot of things right now. A very mixed bag of emotions.

It’s obviously super weird because we’ve been working from home for 4+ months now and I haven’t seen the campus since March… so it doesn’t really feel the same.

Plus, being in this new job the past 6 months has meant that I don’t really see the people I used to work with (with a couple exceptions of friends I’ve taken the time to call for the sake of catching up).

There’s no regret. I’m proud of the things I accomplished there and I’m absolutely ready to leave. I’m sure I’ll miss the people because I already do.

As far as leaving York goes… COVID’s got the whole thing feeling a bit anti-climactic.


So Where Am I Headed on My Entrepreneurial Journey?

At the moment, I’m still making the majority of my income from working directly with clients. They reach out to me, we talk on the phone, I write their resume, cover letter, LinkedIn profile, etc. And yes, that work has substantially picked up and that income is a big reason by I’m feeling so confident about leaving my stable job;

however…

My goal is not to spend the rest of my life trying to write enough resumes to pay all my bills and save for my future. Yes, I do plan to keep doing that, but it’s not the end game, by any means.

The client work is enjoyable and rewarding but it’s limited by my own personal availability. Even if my marketing game was at 110% and I had enough clients for a 2-month wait list, I still could only serve as many people as I had time to serve in a given week/month, etc.

So the plan is, continue the client work, of course (gotta get that bread), and in the meantime…

Continue developing my online course library because that’s where the exponential growth is possible!


As you may know, I launched my first online course “How to Write a Winning Resume and Land Your Dream Job” about a year and a half ago on Skillshare and I’ve now had over 1,800 students take that specific course. I’ve created 6 other courses that have amassed over 900 students between them.

I’ve also licenced these courses to a number of other platform (including a Taiwanese company that is currently translating the course content), so income in starting to trickle in from those other sources as well and I’m very excited to see where all that goes :)

Currently, my online course income is making up about 25% of my monthly income, but I’d like to get that up substantially and I’ve got some big ideas for doing so… one of which is a Super Course which I’ll be officially announcing in a couple of weeks!!!


In Summary, I’m Feeling…

A lot. I’m feeling nerves, I’m feeling extremely excited, very motivated, a little sad, slightly scared, very free, eager, happy, stressed, relieved… a whole love of everything… except doubt. I feel completely 100% comfortable with this decision.

To all those who have supported me along the way through offering encouragement, sending clients my way, watching my video courses, sharing my social media content, checking in on me, thank you! I really appreciate it :)

More updates to come!


DOES YOUR RESUME NEED AN uPGRADE?
DOWNLOADMY FREE e-bOOK!

how to write a winning resume e-book cover

Land Interviews
and Get Hired!

Enter your email and I'll send you the FREE e-book!

    We won't send you spam. Unsubscribe at any time.
    Powered By ConvertKit