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7 Lessons from My First Year as a Full-Time Freelancer

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In May 2015, after 7 years of freelancing on nights and weekends, I quit my day job to freelance full-time. The first year flew by and amazing things happened. I wrote a book, got engaged, landed my biggest projects ever, worked with my best clients yet, relaunched my website, and doubled the size of my newsletter.

But not everything was perfect.

I had to fire a client and reimburse another one. Some leads were lost due to poorly executed sales pitches while I struggled with time and project management. I didn’t know how to set up my finances correctly and got crushed in taxes too.

So today I want to share 7 lessons I learned during my first year of full-time freelancing to help guide anyone trying to “making the leap” away from their current job.

1. Look Before You Leap

If you’re thinking about “leaping” away from your old job into a freelancing career, stop. This critical step is where most freelancers fail. Hold on a little longer working 9-5 and work some extra hours in the evenings. Start by reading some books and articles about freelancing.

Think about it… you don’t want to leap away from your day job into self-employment. Does that sound safe? Instead, you should be building a bridge in your spare time until it’s sturdy enough to walk across. Quitting your job and starting a business should be calculated, not careless.

Make sure you’re pursuing full-time freelancing because you want to freelance, not because you’re sick of your 9-5 job. A false motivation can quickly lead to failure.

Take on side projects in addition to your day job. Work 50 – 60 hours a week for 6 months. Find out how much time and effort it will take to get new projects and clients before waving goodbye to your salary. Not enough time for that? Full-time freelancing might not be for you.

You won’t always have to work that much, but if you aren’t willing to put in extra hard work for an extended period of time to get your new business off the ground, full-time freelancing might not be the right career choice for you.

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Once you’ve gained traction with part-time freelancing, strive to make your transition into full-time freelancing as smooth as possible. Again, this transition should feel more like walking over a bridge than “leaping” off a cliff and hoping your parachute opens.

To build your bridge, you’ll want to have some clients lined up before you put in your two-week notice. That’s why freelancing part-time first is so important.

You should also be getting new leads on a regular basis and have a reliable network of people you can reach out to for new work. Lastly, you need to have a great web presence that can help drive leads toward your new business.

2. Treat Yourself Like a Business

It took me a few months to grasp that I now owned and operated a business. When you’re one-person in size and don’t have a “business” name, are you really a business? Yes, you are.

I thought the simplest business you could have was a DBA, but it’s actually a sole-proprietorship. Once I trained my brain to treat myself like of a business, I started holding that business to higher standards and my career began to flourish.

I started to be a little more firm with clients who didn’t want to pay upfront, scoffed at my prices, or asked for too many revisions. This mental shift started impacting my day-today operations and decision-making in a positive way.

3. Practice Discipline

Do you have dreams of working from home for 15 hours a week and doubling your income? It’s not going to happen (at least not anytime soon). Working from home is a highly sought-after freedom these days, but it’s not all it’s cracked up to be and it’s certainly not for everyone.

Overall, I work fewer hours than before, but my mind is constantly thinking about my business even when I’m trying to relax. Time management is a difficult discipline.

It’s often difficult to focus when you feel like no one is watching you and you have weeks before your next deadline. Procrastination can set in quickly if you aren’t careful. It will take an enormous amount of discipline to stay focused, but it’s also something that can be improved upon over time.

I also find myself working from local coffee shops and libraries for a change of pace and scenery (I wrote this article from a Starbucks 20 miles away from my house). It’s nice to see other human faces, listen to crowd chatter, and sit in a different chair. Every seat offers a new perspective.

Working remotely can get lonely even if you have an independent personality. Be prepared to find alternate work spaces and invest in social activities.

4. Experiment (A Little)

I was hesitant to try new things with my business after quitting my job. If I made a mistake now it would mean losing my only income when previously I had my salary as backup. I decided to overcome that fear and try anyway. Some things went well, others did not.

My first big client as a full-time freelancer (one that helped me transition into my career) ended up paying me $7,000 less than they were supposed to. They even held my last payment hostage for a while. Part of that was my fault for failing to align our expectations properly. I learned my lesson and now require that my clients pay upfront and sign contracts.

Next, I tried selling my first strategy or “roadmapping” session to a new client. Essentially, I charged them for the upfront strategy and planning work that I normally include in the proposal should they choose to hire me.

Unfortunately, the client wanted something different than what I was willing and able to deliver. I recognized this early on and decided to refund them the 100% upfront payment they made and refer them to another freelancer. There were too many red flags. It wasn’t easy to turn away work, but I knew it was for the best.

5. Leverage Retainer Agreements

A few months later, I got my biggest project yet. Then, one of my clients hired my previous client and they collectively hired me for another big project (talk about networking!). I also continued to work on a retainer basis for an existing client who was a reliable source of income during this transition period.

There’s nothing more valuable than having predictable income when you’re a freelancer. Retainer agreements offer just that. Establishing even one such agreement with a client can dramatically reduce the amount of risk and stress involved with your transition into a full-time freelancing career.

6. Create, Iterate, and Improve

About halfway through my first year of freelancing, I decided to write a book. Just a few months later, I reached that goal and published a 55 page eBook called Kickstart Your Freelancing Career.

I also launched a new version of my website and doubled the size of my newsletter (which has since grown to over 1,000 subscribers). I even switched email marketing platforms and automated my newsletter to save time and provide a better experience for my subscribers.

My first year of freelancing was all about growth, organization, and optimization.

7. Grow, Organize, Optimize, Repeat.

I knew that in order to grow my business I needed to save as much time as possible. Every time I tried something new or improved something old, I optimized it as much as possible. I also identified common tasks that were taking up my time and looked for ways to simplify or automate them.

For example, I was responding to more and more project leads each week. After a while, I noticed that I responded to each one in almost the same way.

So, I created email templates that let me draft and send emails in seconds. Those templates dramatically reduced the amount of time I spent writing emails while making them more consistent and professional.

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As my newsletter continued to grow, I knew I needed a way to add more dynamic forms and promotional content. When I relaunched my website, I focused on the blog section and made sure that it would scale for 6-12 months in the exact ways I needed it to. That eliminated the need for me to write custom code for each new form and feature.

When you’re trying to grow and improve your own business, it’s important to optimize it as you go. If you don’t, you’ll risk burning yourself out. Take a look at how your specific business is growing and find ways to save time by optimizing or automating your most simple, repetitive, and time-consuming tasks.

In Conclusion

Full-time freelancing is a challenge. For most people, it’s much more demanding than they expect. It takes tremendous discipline. Before you quit your job, freelance part-time to see if this is the right career choice for you. Make sure it’s the right timing too.

The more calculated, strategized, and planned your transition can be, the more likely you’ll be to succeed. Want to learn more about how to transition away from your current job, raise your rates, get more clients, and find better project? Check out the freelancing resources I have available on my products page.

Last updated on April 13th, 2020

About Matt Olpinski
I've been freelancing since 2009 and have worked with over 100+ clients including some of the biggest brands in the world. I later started my own company Matthew’s Design Co. and now teaches 50,000+ freelancers each year how to succeed through my personal blog, newsletter, and community for freelancers.