My Freelancing Journey To Date

You could say entrepreneurism is in my blood. My dad started his own business right out of college and worked three jobs, sleeping only a few hours each night, to get it off the ground. That was when having a capital to start a business was nearly a requirement — before the digital age when you could start a business for $0. My older brother has a keen eye for knowing “where the money’s at” and created his own LLC to begin contracting out dental sales services. My mother runs a Pilates studio out of her basement. And my little brother is on his way to becoming a CPA on the side.

I’ve always known I would own a business. When I was in third grade I got a fish for Christmas and named it, “Client”. What kind of 9 year old kid names their fish client?

My imaginary play was either running an “Elf Workshop” at Christmastime and ordering my little brother around or running a “restaurants” and fetching my parents snacks from the cupboard. What a weird kid, right? (Spoiler alert, I’m an even weirder adult).

In high school, I would often be writing up random business ideas in the corners of my notebooks instead of paying attention or creating marketing plans for random brands during my study hall. I didn’t realize how strange this was at the time but looking back really makes me go, “What on earth was I thinking?”

Once I entered college, that’s when I really launched into my entrepreneur era. I’m going to take you on a journey, year by year, of how I’ve progressed in my journey. And believe me when I say, I know this is still only the beginning.

2015

I began college this fall and by the end of my first semester realized my school didn’t offer anything remotely close to what I wanted to do. In retrospect, I should have just gone for business, marketing or entrepreneurship, but that’s just the irony of forcing 18 year old kids to make big life decisions.

2016

I considered transferring, then decided to just get a somewhat relevant degree and self teach myself the rest. I signed my major of Journalism with a concentration of PR in my second semester of freshman year, mapped out a class schedule to get myself out in four years, and then created a learning plan. I went to class every morning and would spend my afternoons in the University Center teaching myself how to make a website, SEO best practices, social media best practices, email marketing, and more. My mom and I also launched a blog, Inspirational Nectar, in the fall of 2016.

That summer, I did an internship in PR and quickly realized I wanted nothing to do with PR.

2017

I took on my first client, a friend of my parents who owned a hair salon. I redid her entire website and was shocked with how pleased they were. I was a student, waitressing at a local pub on campus, and in free time (when I wasn’t partying, let’s be honest) I was teaching myself every possible bit of information my brain would accept.

I went back to the same internship because no one in the digital field would take me on. They saw I wasn’t pursuing a career in Digital Marketing or Marketing and weren’t willing to take a chance on me. “Come back in a few years,” many of them told me.

2018

I was still serving at the pub, self teaching, and starting to get really, really bored in my university classes. I was getting antsy to apply some of the knowledge I’d been learning from Google and YouTube. So, I started wandering into businesses on campus and asking them if they needed help. I offered to work for free in exchange for a portfolio piece.

One of these businesses was a protein shake shop and became one of my proudest case studies. The strategy I presented was UGC (user generated content). This was well before UGC became what it is today. We incentivized students to post a photo of their shakes on Instagram and tag the shop in exchange to be entered into a drawing for a free shake. The shop took off and continues to rely on UGC to this day. They’ve also opened other locations and apply the same strategy.

Summer of 2018, I landed an internship with a digital marketing agency, learned the in’s and out’s of Hubspot and was finally able to apply so much of what I was teaching myself. The company was called Web Ascender and to this day, I think the people mentoring me that summer were some of the sharpest and honest marketers (sometimes hard to come by).

2019

Web Ascender kept me through my senior year of college and I happily quit my waitressing job. I was horrible at waitressing. Truly horrible. I would constantly get in trouble for how I spoke to customers. If people were rude to me, I would get so mad I would just ignore the table for like 20 - 30 minutes. I have the utmost respect for anyone in a customer service role and especially those who work in the food/bev industry. Be kind to your servers, please.

Early in 2019, I took on a paying client not in my network. My dad immediately sat me down and told me to open an LLC, explaining how important it is to protect myself and my assets. So I made my business official in February of 2019.

I graduated in May 2019. At this point, I had taken on some small Upwork projects, but mostly paused my business in lieu of graduation, moving to a new city, and starting a full-time job. I made the difficult decision to leave Web Ascender and work for a boutique agency in Grand Rapids, MI. It felt important to me that I really push myself in the first year post grad.

2019 was one of the most trying years of my life so far. And part of it was my job. My first post grad job taught me so much — how to deal with unhappy clients, how to set boundaries with clients, and most importantly, how to prioritize your mental health over your job.

2020

The year of the pandemic. I was one of the few who did not get laid off and for that I am forever grateful. I did end up quitting the agency and going into a corporate position. This decision was mainly for my mental health, but I also desperately needed to make more money.

I slowly got back into freelancing (although I never fully stopped, I just stopped seeking out new clients) and took bigger gigs on Upwork. I experienced my first *impossible* client and dropped a client for the first time. Plenty of content on this coming your way in the future.

2021

This is the year I moved to Charleston. I needed a change, badly. I had three freelance clients at this time and wasn’t sure if my company would let me stay with them. But I knew I needed to do this for myself, despite everyone telling me it was a terrible idea. (Spoiler alert: it ended up being the best thing I’ve ever done for myself).

While I was planning this move, I also took on a new freelance contract. This company was based in Hawaii which meant we had a big time difference. And boy, did they take advantage of me. My day would start around 4:30 a.m., I went to Planet Fitness and worked out, came home and got ready, worked my full-time job 8-5pm, did client emails, ate dinner, hopped on a call with the Hawaii company from 9-10pm and stayed up late into the night finishing up their demands for that day. I was miserable because all I did was stare at my computer. But I was terrified of losing the income from my full-time job when I moved to Charleston.

Things have a way of working out. My company allowed me to sign a remote contract (3 DAYS BEFORE I MOVED. Literally 72 hours before I was driving down to Charleston) and stay on full-time. So I packed up my stuff and my cat, Lady, and made the trek 15 hours south to palm trees, sunshine, and the ocean. This was something I had dreamed of ever since I was a little girl. It’s now three years later, sometimes it still doesn’t feel real.

After moving, I parted ways with the Hawaii company. I took a step back from freelancing, keeping a couple of my smaller retainer clients, but realizing I wanted to settle into my city and breathe for a moment.

2022

This year, I switched teams at my corporate job and got promoted, and really got back into freelancing. I hit the Upwork platform hard, took on tons of projects and made the most money from my business I ever have. I also realized how much I wanted to pursue project management and resolved that in 2023, I would get my PMP certification.

2023

2023 was incredible. I found clients who really jive with me and care about me as much as I care for their brand. I obtained my PMP certification (as of Dec 16 — talk about coming in under the wire). I’ve also started pulling in more money from freelancing than my corporate paycheck. I’ve been working my butt off, but it’s rewarding work.

I’ve also seen a shift in the people around me. In the past, people didn’t give my business the time of day. It’s been apparently obvious not many people believe in me. But I have always believed in myself, even on the hard days when my imposter syndrome is at it’s worst or I have panic attacks from the, “What in the world am I doing?”

In 2023, I saw people start to realize how serious I was about my business. Ask genuine, thoughtful questions and show more respect towards my business. And although external validation cannot be what I rely on, it’s been rewarding and confirmation I am on the right track.

What’s next for 2024?

There is so much happening in 2024 for my business. Stay up-to-date on my content which I am reluctantly going to dive further into (I do not have the confidence to be on platforms but I’m doin it!). So go easy on me, please.

If you like blogs, my next blog will be published on Saturday, Jan. 20. This blog will be in the format of a “guide” to help anyone pursuing freelance drill down into what niche they’d like to focus on.