How I Unexpectedly Earned $72,246.98 During My First 9 Months of Freelancing

2014 was my first year going all in as a freelancer; I ended up earning over $72k by the end of the year, unexpectedly.

In the video above, I share what I did that was so effective during and before that first year, as well as sharing my story on how I got there and how it unfolded.

By the end, you'll have some tangible ideas and actions you can take to either launch into freelancing, if you have not yet started, or to super charge your freelancing income.

These are the systems and habits that have enabled me to turn that $72k number into a fraction of what I earn now.

Let's rewind.

The Story

I had a stint of freelancing right after high school doing computer animation and then again after I moved to Atlanta in 2005 as a computer tech support onsite technician.

I ended up abandoning freelancing to launch and run my marketing company, which I ran and built for seven years until 2014 when I shut it down. The reason I shut down my business was because I knew running a marketing agency with excellence was difficult and I had to be fully committed or it wasn't going to continue working out. I decided that having a marketing firm was not what I wanted to do when I grew up, so I decided to close up shop.

I didn't know what I was going to do next. In fact, I assumed I would have to get a traditional job and become an employee, something that I didn't want to do. Unexpectedly, within a month of shutting down my business, I had multiple freelancing projects. With a wife and kids, I leaned into the opportunity since I was earning an income. I think of freelancing as having chosen me and I decided to choose it back.

By the end of the year, I had earned over $70k by applying the lessons I had learned on my business journey for my freelancing business. And it worked. With this success, I decided in 2015 to master freelancing and figure out how to maximize my success on this vocational path. I succeeded in increasing my annual income to almost $100k. The following year, I began mentoring other freelancers on how to succeed. And in 2017 I published the blueprint for how to do this in my book, Path of the Freelancer which you can grab on Amazon.

That is the short version of my story so let's walk through the milestones and let me share with you what I did at each point that helped me succeed.

The Bear & Our Duty

I decided to shut down my company six months before I did. That gave me a transition period.

There's an idea I have which is called running from the bear. The bear represents the reality that is coming for us. You could think of it like the Terminator movies where the Terminator keeps coming and Sarah Connor keeps trying to get away.

My wife was a stay-at-home mom, so we were a single-income family. This means what I earned is what we lived on. For me, this created a motivational fire to make stuff happen. There were also things I wanted to pursue but would probably have not made money, so I had to set aside my desires and take responsibility for my obligations (which my success would later enable).

So, I had two key ingredients: my desire to flee the bear and a sense of duty to provide for my family.

These are powerfully motivating forces that you cannot underestimate. I've had many freelancing friends who have had a working spouse earning more than they need to survive. Without that bear, they struggle to be motivated to do the hard things required to escape the bear.

On the flipside, I've had freelancing and entrepreneur friends who don't have that sense of responsibility for their family and they pursue things that are not contributing. Without this duty, it can be hard to have a sense of purpose to do hard work.

Now I don't say these things as a condemnation because I've been both of these people many times and am likely to be them again at some point in my future. I say them to clarify the dynamics you may underestimate in what's holding you back from succeeding.

Community Activity

In January 2014, I had three months left before I shut down my business. I had a strong sense that finishing and transitioning was not something I could do by myself and that I needed to involve my community. So, I decided to actively engage in my community.

I decided I would meet, in person, without an agenda as many people in my community as I could. This ended up being around a dozen breakfasts, lunches, and tea get-togethers per week. There was no agenda to try and sell them something or get a job. I simply wanted to catch up. And I shared about the journey to decide to end my business and how I didn't know what was next. People shared their stories, gave me advice, and connected me with other people and resources. Over the three months it ended up being over a hundred people, some I knew well others whom I only knew at a surface level. I was humble and open.

Beyond these in-person meetings, I also called and emailed several other people each day.

One of the things I underestimated was just how important is our existing community and network. As part of growing my marketing company, I did a lot of networking in the first several years. I probably met over 10k people and went to sometimes a dozen networking events in one week. So, I had built a large network and now I was diving deeper into those relationships.

Based on where you are, you may have to do the networking step or you may need to take the relational approach and go deeper. Either way, constant activity is key here. And for me, that lasted 3 months.

Active Online

One other thing I decided to do was blogging regularly. When I looked back, I regretted not having and maintaining a personal blog. So, I committed to getting the blog up and running and posting multiple times per week. And I shared these as a weekly email and across my social media channels.

This online activity complimented my offline activity for a fusion and benefit of both. The online activity did prove valuable. Multiple people ended up working with me directly because of that activity which I continue with to this day.

A Bundle of Projects

Within a month of shutting down my business, I had a full plate of freelancing projects. I didn't seek them out, but they came my way. Since I needed the income, I leaned in. Pretty much all of the projects at first came from people I already knew. Some wanted to work with me before I went to the next thing. Others had business needs I could help solve. I was off to the races.

One of the things I learned from the difficult choice and journey to shut down my business was the importance of focusing on the work in front of me, and not getting distracted by the future, particularly an ongoing pursuit of the next thing. This ties into the idea of finishing well.

Once I started getting paid for freelancing projects, I made the choice that I would focus on trying to find the next project and would instead focus on doing the best work I could for the client. I reasoned that if I did good work, clients would keep working with me and refer me to others. And that's exactly what happened.

My reputation preceded me and I ended up getting all types of awesome projects. I even built a reputation with some of the HubSpot staff, whom I never met, who referred small business clients my way. In my book, Path of the Freelancer, I refer to these relationships as rainmakers.

As a freelancer, I billed hourly in what would become batches of ten hours at a time. In 2014 I logged and billed 1,032 hours. My rate was $75 per hour to start although some clients got a better rate in the early years.

The Recap

There is more to the story, but that is a good place to stop and recap what we've covered so far. To succeed as a freelancer as I did, I'd recommend planning for what I experienced over two years instead of 9 months unless you've got some advantages that will accelerate it.

To succeed as a freelancer, you will need to figure out how to integrate the bear as a motivational force. And, you'll have to ask yourself about how you think of your provisional responsibility for yourself or your family. These two dynamics will be key for staying motivated.

Next, you'll need to lean into full activity both online and offline. I'm extroverted so the offline part is easier for me to do. If you're introverted or the idea of meeting people and networking terrifies you, you'll need to figure out how to approach this in a way that works for your personality style. This is one reason why the bear and duty are important. If you don't like doing something, the bear helps push you to do the things you'd rather avoid because you'd rather do the hard thing than be mauled by the bear.

As far as online activity goes, pick your medium. It could be YouTube videos, a blog, or an audio podcast. It could also be focused on social media activity on LinkedIn, Facebook, or Instagram. Whatever it is, pick one and do it consistently while not worrying about perfection.

And lastly, when you start getting clients, do excellent work and build a reputation as a reliable and talented freelancer. It will organically lead to more work from your existing clients and referrals from your racing fans.

And, if this has been of value to you, grab a copy of my book Path of the Freelancer. I dive into the ideas I've shared in this video in further detail as well as many things I skipped over.

I want you to succeed as a freelancer so, tell me what you think about what I've shared and ask any questions you have about freelancing.

My Story Update: A Note On This Post

This video is an experiment as it is my first video made specifically for YouTube (as opposed to repurposing content I make for other channels). I wrote this blog post as a script to follow, and then I recorded the vlog. I'm publishing it as a blog post after the fact, and have also distributed it as a podcast episode on the Share Life podcast. I'll slice it into a handful of reels to help promote the main video as well.