Path Of The Freelancer


Jason is a former business owner turned full-time freelance professional working from his website, and the author of “Path of the Freelancer”.  We recently had the chance to speak to him and he was kind enough to share his remarkable story.

Whether you’re just getting started or are years into your freelance career, Jason’s story and wisdom are definitely filled with a lot of takeaways you can apply on your own freelance business.


How did you get into freelancing?

I’ve been involved with freelancing for a couple of years but it wasn’t until I closed my marketing company of seven years in 2014 that I decided to go full-time.

When my business ended, I wasn’t really sure what I was going to do next, but within a month, I had a number of projects land on my plate.  That’s how my freelance career started.

The projects unexpectedly kept coming in from existing relationships and previous customers eight months later.  It was then that I realized that freelancing was a financially sustainable path.  Since things were working out, I knew it was time to embrace this new path.

While the quick success may be considered highly unusual, most of the gigs I got came from the relationships established and grown when I was still running my marketing agency.

I was also transparent with my community about the transition I went through.  Prior to the end, I spent three months meeting and calling people, blogging regularly, and staying active on social media. The fusion of these activities provided a strong foundation for me to succeed as a freelancer.

As a business owner who started a company on creative services (video production and web design), I also expanded my skills and abilities to include project management, business development, and team building.

As a freelancer, I dropped the services I was not good at and concentrated on those I excelled in.  Today, I help small digital businesses grow their income and teams.  I work at a strategic and tactical level by making success happen for these businesses.

What prompted you to start a freelance business? 

Unlike many freelancers who pursue freelancing for its benefits, I believe freelancing chose me instead, and I chose it back.  One of the common misconceptions potential freelancers fall for is that freelancing will give them what they want while getting past the downsides of what they were doing before.

The reality is, freelancing is hard.  It usually exaggerates the things we don’t like and can become equally imprisoning as what we were doing before.  To fully enjoy the benefits of freelancing,  you must not only pursue it, but also learn to structure it in a way that empowers instead of enslaves you.

With a well-structured freelancing career, I experienced financial growth, a lighter workload, and a flexible schedule that allowed me to pursue side projects and other future endeavors.

It was totally different when I was running a business.  Back then, I had to sell enough to sustain both myself and my team. Sales today have become a piece of cake, so to speak.

In my pursuit of financial margin and debt reduction, I’m also putting my family in a position where we can enjoy a large financial cushion. This will help us support our lifestyle and meet our future goals.

The freedom that comes with freelancing is no doubt attractive, but it requires a ton of hard work and dedication to bring the vision to life.


What was the inspiration behind “Path of the Freelancer?”

My first year of freelancing was all about survival because I was still testing if it was a viable source of income.  After embracing it, my next goal was to become really good at it.

I took the systems, insights, and experiences I had from business ownership and applied them to my freelancing career.  By treating my freelancing career as a business, I was able to quickly set up a powerful context for me and my family. Other freelancers took notice and began asking me for advice.  They wanted me to share with them how I overcame all the challenges I went through.

They also constantly asked me to write a book.  At that time, I was wondering how I could pursue a financially sustainable writing career.  This book was my first step in accomplishing that goal.  With the demand and a personal reason to move forward, I began the eighteen-month process of creating an action-oriented book that could quickly empower freelancers to succeed in their respective careers.


Tell us a bit more about the book.

The book revolves around eight achievements freelancers need to attain to succeed.  The final achievement is focused around our legacy by teaching others what we’ve mastered.

When I was writing the book, I met with a group of freelancers for a year.  I shared with them the book’s content and asked for their feedback and suggestions for improvement. They were empowered as freelancers and they helped me refine the book and come up with a better product – one that aims to help the next generation of freelancers.

This book was my way of living out this final achievement.  I don’t have the capacity or time to train and coach freelancers, but with this book, the number of people I can create an impact with is limitless.


How has publishing the book helped your freelance career?

This project  provided me with an avenue to learn more about writing, publishing and promoting a book.  Since writing is a road I intended to take, these lessons were priceless.  I’ve also proven that I can do it, which was a big plus in boosting my confidence.


What’s the hardest part of building a freelance business?

I have a fairly steady income and client base.  Even with that, we still have our share of ups and downs.  The downtimes can be especially stressful.  It’s the biggest reason why we’re aggressively trying to pay off our debt and save money.

Another recent challenge I had to deal with revolves around limiting the projects I commit to.  I don’t want to work every day and all the time, so I made sure that I set clear, healthy boundaries in terms of work times and client limits.

Projects can sometimes overlap and go beyond these boundaries, so I leverage resources like FreeeUp and some of my freelancer friends to help get things done and keep within these boundaries.

Work overload facilitates focus, which is crucial when we’ve got an array of activities to work on.


Do you have any advice for those who are just getting started with their freelance business?

The first thing you need to do is to fully commit to freelancing.  Always believe that when you’re short on budget or active clients, you’ll find a way to get another project instead of looking for a job. Fully committed freelancers do what it takes to make it work and they never quit.

Second, get clear on what you’re offering and package it for easy communication.  It’s difficult to sell when you don’t know what it is you have to offer and the problem it solves.  Keep in mind that it doesn’t have to be perfect and it will evolve, but start with the clearest version you can.

Lastly, get active. Meet people in-person regularly and do it without any agenda or expectation.  People who care about you will want to help you grow your freelancing business.  I would also recommend that you consider blogging regularly and staying active on social media.


If you could do it all over again, would you still go with freelancing?

I definitely will.  In fact, I would probably skip the seven-year journey I spent creating and launching a marketing company.  Make no mistake about it, that journey prepared me for success nevertheless, so I’m grateful it worked out.

Freelancing allows me to earn the income we need and want while also providing enough margin and freedom to explore life outside of work.  What more can I ask for?


What’s next for you in terms of business and life?

As I mentioned earlier, I work with small business owners, so I’m currently writing my second book specifically for small businesses who are struggling to achieve their goals.

How do they become better leaders? What do they need t0 do to build stronger systems? How do they bring their teams along?  I’ll also provide them with a plan that will help them navigate the chaos and create an organized and scalable business.

Outside of the book, I’ve got several other goals for the year that include paying off our minivan, engaging more with my four (soon to be 5) kids, get more physically active, volunteer at my church, and publish blogs to hit a total count of 400.


Final Thoughts

Jason may not have found fulfillment through his marketing business, but the lessons he learned as a business owner have certainly been instrumental in the success he has found with freelancing.

With the lighter load, flexible schedule, and the time he can now spend with his family, he has truly embraced freelancing enough to make it a career. Apart from these really cool perks, freelancing has also allowed Jason to start writing and publishing books.

His success is nothing short of motivating.  Like every successful endeavor, however, hard work and perseverance are ingredients that should always be present.