Lessons Learned From Earning $72,246.98 During My First 9 Months of Freelancing

2014 was my first year going all in as a freelancer. And at the end of the year, I had earned over $70,000 unexpectedly.

In the following video, I'm gonna share with you what I did that was so effective, and I'm also gonna share with you my story of how things unfolded. And, I'll share how I ended up getting to that financial outcome. By the end of this video, I want you to have ideas and tangible actions you can take to either launch into freelancing, or if you're already a freelancer, so that you can take advantage of the opportunities before you and supercharge your income.

The mindset, habits, and systems I'm going to share with you in this video are what enabled me to earn the $72K+ during my first year of which I continue to build upon. Before I dive into those ideas, let's rewind. 

My Freelancing Story

I had a stint of freelancing shortly after graduating high school where I was doing 3D animation for different projects on several TV networks. I also had a freelancing stint after I moved from Flagstaff, Arizona to Atlanta, Georgia in 2005 where I was a computer tech support tech. I was a technician who was going to to people's houses and to places of business and it was servicing their computers and their networks and trying to help them. I ended up abandoning freelancing to launch my marketing agency in 2007 which I ran for about seven years until I shut it down in 2014. The reason I shut down my marketing agency was that I knew that continuing it with excellence was going to require a lot of work.

I was thinking about what is it I wanted to do vocationally and did I wanted to own and run a marketing agency. And that wasn't what I wanted. So I decided to shut it down. I didn't know what I was going to do next. I assumed I was going to have to go get a job somewhere or be an employee at someone else's company. Unexpectedly, within a month of shutting down my company, I had all these freelancing projects and I leaned into it. I had a wife and kids and I had to provide. So I leaned into freelancing.

I think of freelancing as having chosen me and I simply chose it back. And throughout 2014, I leaned into it, I figured it out, and by the end of the year, I earned over $72,000. It was an awesome accomplishment, and I took the lessons that I had learned from my business and I applied them to my freelancing, which was a business of one. Which is one of the challenges I think a lot of freelancers struggle with is they think of it as simply a job doing work for a company, but if you treat your freelancing as a business, even if it is only a business of you, that mindset is the type of thing you need to succeed as a freelancer, and that's what helped me succeed.

With this success, I decided, you know what? In 2014 at the end, I had earned this income, I'm gonna lean into this, and I'm going to master freelancing. I'm gonna figure it out, and I'm gonna conquer it. And that's what I did in 2015. I took what I learned in 2014, and applied it to my freelancing in 2015, and I did even better, earning more income. And I've continued to do that year over year over year.

But in 2015, after that, year that followed, 2016, I had other freelancers that were asking me, how did you do this? How did you overcome this challenge? What did you do? And so I started to mentor them and share with them a blueprint. That blueprint is in a book I wrote called Path of the Freelancer. It has everything I'm sharing with you here in this video and more, more details. This is the blueprint I've used to not only generate $72,000 in my first year of freelancing but more than double that in the years to follow.

That's the short version of my story.

The Bear & Duty

Let's go ahead and dive into the milestones at each point and what are the specific things that I did that helped me succeed and flourish as a freelancer.

The first thing I wanna talk about is what I call the bear and our duty or our responsibility to provide.

I decided to shut down my company six months before I shut it down, and that gave me a transition period. So there's this idea I think about, which I think of as the bear running away from the bear. The bear itself is the impending reality. It's the bills that are coming in. Another way to think about it is to think about the Terminator movies, where the Terminator is going after Sarah Connor, and she's trying to stop the Terminator from killing her and trying to escape. So the idea behind the bear is the bear is chasing us. This is reality. This is a financial obligation. These are our bills.

This is all the pressure that we feel that we're trying to escape by earning an income. The bear is a powerful motivating force. You can't underestimate the bear because when the bear is chasing you, can forget when we get comfortable and we get financial margin, you can forget how much the bear motivated us to succeed, how much it drove us to do the things we do. I'm a decade into freelancing and I feel I've had so much success that the pressure has been relieved to such a degree that I don't have that same bear coming at me in the same way. And I have to remind myself and come up with ways to remind myself that the bear is still there. One aspect of the bear for me, for my family, is that we're a single-income family. My wife's a stay-at-home mom. So that bear is a little bit more threatening than if we were a dual-income family. Now, that's the bear.

The second dynamic is...what I think of as duty or responsibility. And so because we're a single-income family, because I have a wife and kids and we have financial obligations, I've got to pursue things that are going to contribute and allow me to provide for my family. And so there's a lot of things I wanted to do. There are a lot of things I love doing even now, but they don't necessarily create the income to provide. And so I had to set those aside, at least for a shorter period, and pursue the things that were earning income so that I could fulfill my duty, take care of my responsibilities, and provide for my family.

So both the bear and duty are powerful motivating forces that we can't underestimate when it comes to the type of pressure that is healthy and driving us towards maybe doing hard things that we might not want to, to avoid procrastinating, and really to help us move forward towards the things that we need to do. So if we're going to freelance, it's going to be doing the things needed to flourish as a freelancer. And these dynamics, these pressures are going to be ones that we integrate and channel so that we can generate the outcomes that we're looking for.

When it comes to these dynamics, I've had freelancing friends whose spouses did work and whose spouses made good money. And that lack of that motivation, that lack of that pressure, that bear, it made it difficult for this person to do the things they needed to do. On the flip side, I've had freelancing friends who pursued things that weren't financially viable and were creating contention and problems in their families because the work they were doing wasn't making money.

Now don't say these things as a condemnation to anyone who might be in one camp or the other, but just to recognize the dynamics at play so that you can lean into them. And I'm a culprit. I've been both of these people. I've been someone who didn't have the bear chasing me because someone else was providing.

And I've also been the person who's pursued things where money wasn't coming in, but I still put all this time and energy into it without regard for the people that it was affecting. And so it's helpful to understand these dynamics so that we can again integrate them, channel that energy into productive outlets, and eventually be able to sort of pursue the things that we love to do, but also the things that make money and provide for our obligations. Once we've mastered that, we set that foundation and we can pursue other things that maybe are more risky or aren't necessarily going to generate the type of result that we might need to pay our mortgage.

Community

In January 2014, I was on the tail end of shutting down my company. And going into that month, I had this sense that I wasn't gonna be able to finish by myself. I needed help, I needed friends, relationships, I needed other people.

So I decided to lean into that community. If that's what I needed, I was gonna dive in. That's what I did for the next three months. I started meeting with people 10, 12 times a week, a lunch, a breakfast. We got tea, and coffee, however they would meet with me. This was before the pandemic, so meeting in person was more of a thing. There were also phone calls on top of the 10 to 12 meetings throughout the week. Sometimes it'd be multiple a day. I also sent out emails, made phone calls, and texted people. So it was just a lot of activity.

And I did that over the three months from January into February and into March. And that was crucial for the success that would come after that. All that activity, all those relationships, all those connections. And the big thing about those meetings and that reach out, was agenda free. I wasn't looking to sell anything. I wasn't looking to get anything from anyone. I just wanted to meet with them and catch up. How's life? What's going on? It was also an opportunity for me to share with them what was going on in my life. The fact that I was shutting down my company, how I was processing that, the fact that didn't know what I was gonna do next, getting their advice, getting their feedback, and it was just a great learning opportunity.

I leaned into humility and I just went with it. The community was a huge part of my success and one of the things I didn't realize at the time was just how much building community, even before this event happened, how much it mattered. When I moved from Arizona, I came from Flagstaff, a little city in the mountains, and I moved to Atlanta, Georgia in 2005 and I ended up launching my marketing company in 2007.

I didn't know how to get clients. I didn't know where they were. I started cold calling I started calling people going to businesses and I ended up discovering networking once I discovered that I was like wow, everyone comes to one place and I can meet a bunch of people at once so I started doing a lot of that. I networked so much that probably over several years I met around 10,000 people, which was a lot of people to me.

And this was a great opportunity to lean into some of those relationships. And through those three months where I was doing a lot of activity. I ended up meeting between 100 and 150 people. It just led to all kinds of opportunities. learned, some people shared resources and ideas, some people made connections, and some people ended up becoming some of my freelancing clients unexpectedly. So this activity was just a huge part of my transition and is one of my go-to's whenever as a freelancer I needed to get a lot of clients. I've had a full client load and I've been able to sustain that for years but if something were to happen where I just didn't have enough work that probably my go-to would be going to a bunch of networking events it'd be meeting with people, I'd be calling people, zooming people and getting that activity going. Bing someone who's been in sales when I had my marketing company, I had to sell, find leads look for those projects, and get projects. We had a team and I had a payroll so I had to get a lot more work than I needed just as a freelancer.

So that activity plays a big part of it. Depending on kind of where you're entering into freelancing, where you're at at this moment, it's gonna depend on whether or not you need to just meet with people you already know, contacts you have, maybe go deeper with shallow relationships, maybe you go even deeper with people you know better. The other thing you might have to do is just start networking. Maybe you don't know anyone or you know very few people. And you need to go to some of those events. You need to do some of the activity to establish enough relationships that you can start getting meals, breakfast, lunch, or tea or coffee with some of those people. And so based on where you are, you're gonna wanna generate activity. You just have to figure out which of the two is the better fit for you right now.

Getting Active Online

Now, in addition to getting active, like in person with people, meeting with them without an agenda, the other part of the puzzle was the digital activity. In January 2014, that's when I started blogging.

I'd regretted that I hadn't maintained a personal blog for the previous decade because I've done a lot of things and I felt like I just always had to keep starting over. And having a personal blog, I felt like was an opportunity for me to keep a thread going between all the things that I was doing and to keep that community, that network that I shared about, to keep them engaged and to stay in touch with indirectly and also a scalable way. So getting active online was a big thing.

So I started blogging multiple times a week and then I would share those on social media. And that was huge. In addition to the in-person activity I was doing, the direct contact with people via phone email,, or text, my blog, and social media activity was just another layer to staying connected with people, keeping in touch, and letting them know what I was doing and just providing opportunities that would then turn into freelancing projects, clients either that month, months later, or years later.

There were some freelancing clients that I've gotten where they followed me for several years before they started engaging with me. So online activity is just a huge piece of the puzzle. Within a month of shutting down my company, I had a bundle of paying freelance projects. And since I needed income and I didn't have any other opportunities, that's what I leaned into. Projects kept coming. They kept coming and they kept coming.

Finishing Well & Building a Reputation

And I made a decision, one of the things that I struggled with when I had my marketing company is I was always looking for the next project. I was always looking forward to the future. And so one of the things that I learned in the process of shutting down my company was the idea of learning to finish well. What does it mean to finish well? And one of the parts of that learning process was understanding that to finish well is to focus on being present in the moment. And so doing what's right in front of me. And so as I started getting these freelancing,

I made the decision not to look for the next project. Instead, I would focus on delivering quality to those clients. I would give them the best work, my best time, whatever I could give them as part of my engagement with them, I was gonna give them 100%. And by doing quality, solid work, staying in communication with them, being accountable, and doing excellence in the work we were doing, I trusted that this excellent work would lead to them working with me more. So clients would continue to work with me and some of those clients would turn into raving fans who would then refer other clients my way. And that's exactly what happened.

I continued to maintain those client relationships and that organically led to new client relationships through referrals and word of mouth. In my book, In Path of the Freelancer, I referred to those people as rainmakers, those are, raving fans of their clients. But I had built such a reputation that I had people at HubSpot, people I had never met that worked at HubSpot that heard about me and they were referring small business clients of theirs that were using HubSpot my way to help them with their website and their email marketing and automation and things like that. And so I had built a reputation with people beyond just my clients, but the clients, the relationships that my clients had, and those became the rainmakers that ended up referring business my way. And some of those referrals ended up being monumentally important to the success and progression of my freelance work.

So as a freelancer, I was billing hourly. In the book, I talk about a system, I call the batch system, where I do batches of 10 hours at a time, which gives the client control over my hours so that they're able to budget and know what to expect in terms of what I'm gonna be billing them. Anyways, I decided to charge hourly. And by doing that, I was able to narrow down, you know, to earn $70,000 to earn the amount of money that I needed to earn, breaking it down into a daily number. This is how many hours I need to do billable hours per client, or just across my clients, but per day, per week, per month, to get to the end goal. And so every day was just about accomplishing that goal. Do I have that many clients with enough billable hours to do that?

And in those early years, I didn't. So I would get all of my hours done and then I would contact my clients and try and get more hours from them or find new opportunities. But across that first year, I earned over $70,000 and there were about a thousand billable hours. That's how I was able to accomplish it. In nine months, I was able to earn $70,000. That was a huge accomplishment. And there were a lot of things that I had in place that I think allowed me, that gave me an unfair advantage, that gave me the ability to launch much quicker than I might have otherwise done.

You may have that advantage, or you may have a different advantage, but what I would generally recommend is not to expect that it'll take nine months, but probably plan around two years. It's probably about two years that you need to be doing the activity that you're doing and consistently delivering on the client work that you're getting to build an income like that and then even beyond.

Recap

Now to recap, let's kind of walk through some of the things we talked about.

So we talked about the bear, we talked about duty. The bear is this force, this pressure that's driving us to earn that income. Like what do we need to have in place? What are the hard things we need to do? Do we have that pressure to drive us out of our comfort zone and towards accomplishing our goal? And if we don't have that, either organically or just naturally, because like in my case, I had a wife and kids and we were a single-income family. If you don't have those things, then you need to think about how could you simulate them. How could you create that kind of tension that you would be driven? And then the second would be a duty thing, the responsibility. And that's something you just need to think about and ask yourself like, are you willing to take responsibility for this part of your life, for the provision of your family, or part of the provision? Maybe it's not taking it in completely. Maybe it's simply about owning some responsibility for what the income that you're going to generate is going to accomplish. Maybe it's simply to take your family on vacation or maybe it's to fund your children's college education, or maybe it's to begin investing in your retirement, something you haven't started, whatever it might be, there are other ways you could create those tension points. I know for us, we wanted to pay off our student loans, we wanted to, we ended up buying a minivan for our family, which we had to pay off, and then we also wanted to buy a house, we saved up a down payment. So those were different things that created that tension, and those are the things that you need to think about. So that's the bear, that's the duty.

The next thing is about activity. We talk about community activity and online activity, fusing them, doing both at the same time, creating that activity, doing it regularly every day throughout the week, in person, at networking events, online, blogging, maybe you're YouTubing, maybe you're podcasting, whatever you're doing, but you're doing that regularly to create that activity. And then the last thing is about focusing on the client work you're doing as a freelancer, on being present with your clients, taking care of them, doing amazing work, and building a reputation that'll allow them to continue working with you and refer you to all of their business friends and colleagues.

Those are some of the things that I applied and learned and that helped me succeed in my first nine months as a freelancer. If what I've shared with you in this video has been of value, I'd recommend that you pick up my book, Path of the Freelancer, and it's designed for you to be able to read through, just go to the piece that you need. Go to the section, it's divided into eight checkpoints that freelancers need to accomplish to succeed and flourish. Figure out where your freelancing is weak or where you're missing it and go to that part. Figure that piece out and just go to the solution that you need today.