It was back in February when I started documenting my experiment from nine-to-five employee to full-time freelancer here on Careful Cents. I started earning a side income — and building a side business — a few months earlier.
When I wrote that first post, I was scared to death to publicly commit to a huge goal.
I declared I would quit my job and go full-time with my digital business by March 2015. Turns out, I didn’t need to be so scared of sharing that goal. I completely blew it out of the water just four months later, and officially went from employee to freelancer in June 2014. In case you’re not keeping track, that’s nearly a whole year sooner than my goal.
But how did I justify making the leap almost a year before the deadline I set for myself? How did I know it was time to go from employee to freelancer?
There were four big things that signified it was time for me to make the leap — and these markers can help you determine your own jumping-off point into self-employment.
1. Do you have an abundance of work?
Throughout the spring, my workload grew exponentially. Every week I completed more tasks and more projects. Every month I picked up multiple new clients. I was in full YES mode, where I didn’t say NO to anyone or anything.
This went completely in the face of most good business advice for freelancers. We ought to be careful guardians of our time, only allowing the best and most fulfilling people and projects to have access to the hours in our days. And we can’t be afraid to turn down work or “fire” clients that don’t respect that precious time.
But when you’re building a side business with dreams of transitioning it to a full-time endeavor, there’s a lot to be learned and gained from saying YES to nearly everything. You won’t fully appreciate the importance of saying NO in your business or to your clients, until you’ve experienced what happens when you don’t say it. You’ll understand exactly why successful entrepreneurs give that advice, and you’ll make it a priority once your business is full-time.
(Carrie’s note: this couldn’t be a more true statement and something I learned first-hand myself.)
And, as was the case for me, you’ll build up an enormous portfolio of clients that will enable you to jump from employee to full-time freelancer. Of course, you’ll also be working insane hours. For me, it was 80, then 90 hours per week near the end.
I didn’t keep all these clients once I did make that leap, but saying YES allowed me to create an abundance of work that gave me the confidence I needed to know I could make working for myself full-time a reality.
It taught me that I could always find new sources of work — and income.
Learning this lesson, and bringing a ton of work with me into self-employment, was the first sign that I was ready to quit my day job and pursue my dream business.
2. Can you provide a sustainable service to quality, long-term clients?
When I started side hustling, I didn’t possess much focus or sense of direction. I was sending out feelers left and right and happy to pick up whatever gig came my way.
This provided a great learning experience, and I quickly understood what I enjoyed doing — and, more importantly, what I did not enjoy. As long as I was firing off applications and pitches and queries at random, I knew I couldn’t turn my work into a full-time career.
I needed to find my niche, identify my ideal client, define my services, and create something sustainable. I worked toward serving high-quality clients that wanted to hire me on a retainer basis. This meant my work (and earnings) would be reoccurring, and I could reasonably expect to develop a long-term relationship with the client.
I also worked to ensure the services I offered were sustainable. This meant identifying projects that my ideal clients were unlikely to ever want to do themselves, and would always want someone else to take care of for them. I stopped offering services that my clients could — or wanted — to do themselves, or that could be handled by someone else on occasion.
When you work in the digital world, there’s always a threat of your work being wiped out next year by some new innovation. I avoided things that were trendy or that had a history of changing quickly, and instead focused on creating offerings that could easily change or keep pace with the online industry.
Taking these steps allowed me build new sources of income on something that I could expect to last for a long time. Knowing my work was based on quality clients interested in long-term relationships served as the second sign it was a good time to go full-time with my business.
3. Are you seeing a positive trend over time?
Since I started picking up work outside my day job, each month that I kept at it only returned more income and more clients. As things snowballed and grew, I kept detailed notes and tracked just about everything that was going on.
That left me with a clear, big picture to evaluate when I felt like it was time to start thinking about quitting my day job in favor of becoming a full-time freelancer. I pulled up all the data I had and what I saw was really reassuring.
My volume of clients ticked up every month — and the majority of the new work originated from people who came to me asking to work together. Although I started picking up clients by cold emailing and responding to job ads and listings, the last few months before I quit my job showed that more people approached me after hearing about my services from others in the industry.
In other words, the real-life connections and online networking I continued to do, was paying off by rewarding me with word-of-mouth recommendations and new clients.
It’s a positive sign for your dreams of self-employment when business picks up because you developed a reputation that drives more clients your way than any active marketing efforts could.
But what about the trend that everyone is much more concerned about? I’m talking, of course, about the money. Did my earnings follow the upward swing of clients?
Yes! In fact, since I started earning a side income in November, each month that followed brought in more revenue than the previous month. In a way, this was a little scary: it would have to level off or drop at some point. But I still felt good about the numbers, especially as in the last two months before I quit my day job, I made more through my business than I did as an employee.
Seeing the positive trend in my earnings provided me the third sign I needed to know I was ready to go from employee to entrepreneur.
4. Do you have a high level of self-confidence?
The last and most important sign that it was time to quit my job and launch my business full-time was something much more intangible than a bigger portfolio of clients, or higher earnings each month. When I realized I had gone from being scared to death of failing, to confident that I could handle anything as a self-employed individual, I knew I was finally ready.
During the month before I put in my two-week notice at my day job, I agonized over whether or not it was time to go full-time with my own venture. There was a steady stream of what ifs running through my mind one day: What if I failed? What if every client I had suddenly disappeared? What if all the prospects I had lined up fell through?
And the next day, my thoughts would fight back: But I’m making more money than I’ve ever made working for someone else. I’m getting emails every other week asking if I have the bandwidth to take on more work. I realized, I was already working full-time hours for my business!
Finally, someone asked me a really important question. They asked, “do you think you can do it?”
When I answered YES, without hesitation — without any little voice in the back of my mind piping up in protest — I knew it was time to officially go from employee to full-time freelancer. I realized I had something much more important than a stack of clients or a steady stream of income.
I had faith in myself and my ability to make things work, no matter what.
Are you thinking of making the leap from employee to full-time freelancer? What signs have you seen that are making you believe it’s the right time?