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In early 2018, I left my company profession in human sources to go on what I then referred to as a sabbatical.
5 years later, I’m a contract author, enterprise coach, and writing mentor.
The in-between is a journey I mirror on typically, and I’m grateful to have the chance to share it with you.
Why I Began Freelancing
I began freelancing unintentionally. Throughout my sabbatical, I launched a weblog that partially centered on private finance.
I made connections throughout the area of interest by way of social media and, after some time, wrote a visitor submit for a outstanding web site within the house.
After I bought paid for my work, a lightbulb went off. If I might earn $50 writing, I might earn $500, $5,000, and extra.
So I instantly began on the lookout for platforms I might contribute to usually. My first regular consumer was Ladies Who Cash!
As just a few {dollars} turned to 1000’s, I noticed I had met the purpose of my sabbatical: discovering a location and schedule-independent option to earn a residing. That approach, I might absolutely present up for myself and people I beloved.
I might work round my life moderately than reside round my work.
Wish to know extra about my backstory? Take a look at this Ladies’s Cash Speak article.

Advantages of Freelancing
Over the last half-decade, I’ve loved many advantages from freelancing — some anticipated, some a shock.
In fact, I’ve beloved:
- Creating my very own schedule, fully accountable for the place and after I work.
- With the ability to scale my freelance enterprise up or down based mostly on the ebb and movement of my life.
- Selecting which shoppers to work with and which assignments to just accept.
However I’ve additionally deeply appreciated:
- Forging relationships with different freelancers and entrepreneurs (they’re your folks, not competitors!)
- Gaining confidence with regards to asking for cash.
- Getting pushed out of my consolation zone (repeatedly!).
- With the ability to absolutely step away from my enterprise for greater than three months when my dad handed away in 2019.
I knew from the get-go that freelancing would supply the liberty and adaptability I wished.
However I didn’t notice how a lot that may matter till my father bought sick. Then, I bought to place every thing else on the planet on maintain to give attention to him, my household, and my psychological well being after his loss of life.
Freelancing gave me the dear present of time.
I additionally couldn’t predict how a lot progress I’d expertise as a small enterprise proprietor.
I’ve met extra individuals and gained extra data within the final 5 years than within the 30+ years earlier than!
Associated: Ought to I Give up My Job to Freelance? [The Pros & Cons]
Challenges of Freelancing
Naturally, my journey hasn’t been all chai lattes and impromptu naps. Regardless of principally having fun with the journey, I’ve additionally handled my fair proportion of challenges.
There have been apparent points, reminiscent of:
- Not having employer-sponsored advantages (particularly medical insurance and a retirement financial savings plan match)
- Not getting paid after I don’t work
- Having to navigate paying my self employment taxes (I like to recommend getting an accountant as quickly as you begin making actual cash.)
- Having to at all times hustle for brand new and higher shoppers
- Budgeting with variable revenue (the feast or famine phenomenon is actual!)
However I’ve additionally skilled some unanticipated hiccups, like:
- Shedding a number of shoppers in a brief interval
- Having potential shoppers specific curiosity in working collectively after which ghosting me
- Coping with tasks that didn’t play out as marketed
- Chasing funds for accomplished work (I believed I would wish a lawyer to gather a number of thousand {dollars} from a consumer. Luckily, it didn’t come to that.)
My greatest takeaways from these challenges are constantly fostering connections in your community and getting all gig particulars ironed out upfront and documented in writing.
That approach, you’ll be able to name upon your circle whenever you run into powerful instances, and there’s by no means any query about how a undertaking ought to go.
Plus, you will have a authorized doc to again you up if a deal goes fallacious.
Learn: Earlier than You Go Freelance, Do These Issues
If I Had To Begin Once more
If I needed to begin once more, would I do something in a different way? A part of me says no, however a part of me says hell sure!
On the one hand, I imagine every thing I’ve skilled has formed me into who I’m.
I like who I’m and assume I’m precisely the place I’m imagined to be (though I’m nonetheless removed from attaining lots of my targets).
However, alternatively, I’m wiser now than I used to be then, and it will be good to make use of that perception to construct a greater enterprise quicker.
So, if we magically went again to February 2018, right here’s what I’d do:
- Write extra visitor posts — and write them sooner. Doing so may need helped place me as a private finance authority and led to gig alternatives.
- Purchase fewer programs and take extra motion. I’ve bought extra programs about on-line enterprise than I care to confess, and plenty of of them sit unfinished and unimplemented.
- Develop passive revenue streams as early as 12 months two. I’m nonetheless making an attempt to get just a few of these tasks going. Had I began in 2019, I could also be amassing a good amount of money from them by now.
- Work extra hours. I’ve loved the liberty of freelancing just a little an excessive amount of… and my funds mirror that!
Sadly, my Delorean is completely within the store, so time journey is inconceivable. However I’m making an attempt to take my very own hypothetical recommendation into consideration now!
Ceaselessly Requested Questions
Right here are some things chances are you’ll be questioning about:
How do you keep motivated to be your personal boss when so many different issues might pull you away?
The reality is – I haven’t at all times been nice at this. There have been intervals the place I didn’t work practically as a lot as I ought to have.
I can title many causes for this (some legit, others not a lot), however the backside line is that my motivation has waned now and again.
After I catch myself in a stoop, I discover that necessity and long-term targets propel me to motion once more. I want money to pay my payments and fund the long run I need, so again to work I’m going!
Has synthetic intelligence (AI) modified your job, and are you frightened about it changing you?
Many freelance writers fear that AI instruments like ChatGPT will finally substitute them. I don’t assume that’s true.
AI can mixture and spit out data in an more and more logical approach. However the computer-generated phrases lack nuance and storytelling.
Human writers can develop connections, stir feelings, and immediate motion much better than the digitally-created copy.
That mentioned, AI instruments will be helpful to writers. They may help generate concepts for additional analysis.
Ought to freelancers have a number of streams of revenue?
100% sure! When you will have a number of revenue streams, you cut back your danger of economic bother when a number of dries up.
Nonetheless, freelancing (sometimes) inherently offers this buffer, anyway.
Every consumer or undertaking is a income. So, you’ll have to consider carefully about different revenue sources you’d like to include into your online business.
Personally, I present teaching companies to new and aspiring freelancers in addition to professionals making an attempt to turn out to be higher writers.
I’m additionally exploring the concept of promoting printables and freelancing-related merchandise.
Have you considered going/gone again to any W-2 work?
I maintained some part-time W-2 work for the primary a number of months after quitting my full-time job.
Doing so allowed me to protect my financial savings whereas I discovered a plan to earn a residing going ahead. Nonetheless, as soon as I began getting a whole lot of writing gigs, I give up these roles to give attention to my freelance enterprise.
Since then, I’ve admittedly contemplated returning to a standard job often as a result of I generally miss the regular paycheck and advantages package deal I had within the company world.
I even bought deep into the hiring course of with one firm. Nonetheless, after I take into consideration every thing I’ve gained from self-employment, it turns into a no brainer for me to remain the course!
Will you shift to a unique small enterprise that you just personal should you get uninterested in/burned out on what you’re doing now?
I can undoubtedly see myself altering gears sooner or later, which is one other wonderful cause to domesticate extra revenue streams.
Writing on a regular basis generally is a grind, so I received’t essentially do it full-time perpetually. Nonetheless, I extremely doubt I’ll ever return to conventional employment.
How do you cease “chasing” cash (taking up an excessive amount of work)?
Simply as there have been instances after I labored too little, there have been instances after I labored an excessive amount of.
After I discover myself chasing cash, I bear in mind why I took that sabbatical 5 years in the past: to find a option to earn a residing and reside my life.
I have to always remember (not less than for lengthy) that the second half is an important!
As my father typically mentioned, “You possibly can at all times make more cash, and you’ll’t make extra time.”
Do you construct in trip time for your self? Do you will have set days off every week?
My schedule is extraordinarily versatile. I take break day after I wish to or when life calls for it.
I try to work 4-5 days every week, however the days aren’t at all times the identical. I depart room for appointments, errands, occasions, sickness, and even mind fatigue.
Since writing is mentally taxing, I’m generally not in the correct headspace to do it.
After I take a trip, I do considered one of two issues. I both work forward and inform my shoppers after I’ll be unavailable. Or, I’ll convey my laptop computer alongside and write when everybody else is asleep. Each have labored properly for me.
What are a few of your finest and worst moments/experiences as a small enterprise proprietor?
Listed here are just a few of my finest moments and experiences:
- Incomes my first freelance {dollars}
- Exceeding my month-to-month company revenue
- Negotiating for extra money (this one by no means will get previous!)
- Assembly my freelancer pals in actual life
- Serving to different freelancers with their enterprise
- Talking at a convention
And listed below are just a few of my worst:
- Chasing a consumer for $6,000 — and being made to really feel insignificant within the course of
- Shedding profitable shoppers that I beloved working with
- Owing taxes after I actually couldn’t afford to pay them
- Watching web sites I wrote for stop to exist (there go these hyperlinks in my portfolio…)
- Doubting my capacity to keep up and develop a enterprise (this sense creeps in periodically)
I’m positive that I’m forgetting many highlights and lowlights. However the fact is, freelancing has given me greater than it’s taken, and it’s completely been a web achieve for my life!
Ultimate Ideas
I hope this account of my journey has given you a glimpse into what to anticipate as a freelancer — each now and within the years to come back. However should you nonetheless have questions, I’m a fairly open guide. Be happy to e-mail me to speak store: [email protected]
Right here’s to your freelancing success!


