Reflections on My First Year of Full-Time Freelancing

Jan 9, 2014

By Carrie Smith

Carrie Smith is a financial writer and community builder who blogs at She's on a mission to help solopreneurs and small business owners earn more money in less time. Find her on Twitter (@carefulcents).

At the end of 2010, my personal and professional life were falling apart. With over $14,000 in debt, I could barely afford a decent apartment and my day job was slowly sucking the life out of me. I felt trapped and needed a fresh start. But how?

That’s when I started putting together a solid freelance writing portfolio and decided to give freelancing a shot.

I wanted to start my own business to have more freedom, no longer answer to someone else’s schedule, and be able to put my social/family life ahead of work. I spent 2 years working multiple jobs while building my freelance business. Last year, I was able to pay off all my debt, quit my day job, and jump into freelancing full time. Here’s how I did it:

I Surrounded Myself with Successful People

Without the support of the community I created around my blog or the other freelancers I met along the way, I would still be stuck in my accounting job. This is when I learned how peer pressure -- whether good or bad -- can affect the entrepreneurial mindset.

Study after study shows that peer pressure is what influences us, and the more accepting a group is of either positive or negative behavior, the more likely we are to do the same thing.

My friends and family still cling to the outdated belief that if you get a steady day job you’re set for life. So if I wanted to set myself apart from that type of thinking I knew I had to surround myself with successful, forward-thinking people.

Whether you’re a newbie freelancer or a veteran looking to up your game, you can use this kind of peer pressure to your advantage.

I wanted to throw in the towel more than once, but I received so many encouraging comments, emails and messages that provided the motivation I needed to keep going.

I Found a Supportive Freelance Community

There are several ways to connect with a like-minded group of people who share your ideals and goals.

1. Seek Out a Local Group

You’d be surprised at the vast array of events and social activities that are going on in your local community. Your local newspaper or event calendar will likely have tons of meetups for freelancers or anyone who’s looking to grow their business.

You can also connect one-on-one at coworking spaces or coffee shops, since these are the most popular places to find other go-getters, freelancers and entrepreneurs.

2. Connect Online Instantly

One of the best things about using the internet is that you can find lots of different groups, organizations and communities almost instantly -- anywhere in the world. Even something as simple as a Twitter account can connect you with anyone in real time.

There are other places like Facebook and LinkedIn groups, membership forums and community boards that you can search out online with just a few types of the keyboard.

What Encouraging Support Did For Me

Now that I’ve told you what a supportive freelance community did for me and explained how to find one, here’s what the right community can do for you:

I felt less isolated and alone

As I mentioned, when I finally woke up and realized it was time to get my finances under control and pay off debt, no one in my circle of friends or family understood. In our society today, living with debt is an accepted norm. Changing your financial mindset goes against the grain, so is often challenged by others.

This can lead to feelings of isolation and be very discouraging. But if you’re able to surround yourself with a different group of people who understand what you’re going through, you’ll feel less alone. They can encourage you, and ensure your chances of reaching your goal.

I solved my own problems

Sometimes hiring an expert is just what you need to find that balance in your life. But at other times you don’t want to be “coached” or spoken down to, so having a close-knit community of peers can enable you to solve your own issues.

When other people are experiencing the same type of problems you are, there is a unique emotional connection that’s different from any support you can get from a professional or expert.

I found a safe environment to open up

Seeing others who are dealing with the same adversity and making progress in their lives is inspiring and encouraging. A community is a safe place for someone who needs to talk about intensely personal experiences, struggles and thoughts.

Many times, talking to an expert can be very intimidating, but with a like-minded community, the members and peers treat each other as equals. You may view it as if you’re all in this horrible, discouraging place together, which can make you feel more comfortable about opening up.

I gained more confidence

Talking to other freelancers can reduce your anxiety, improve self-esteem, and create a sense of overall well-being. When you feel more confident about your life and your direction, you’ll be less likely to give up.

Additionally, you’ll have higher self-esteem and a clearer mind, which leads to more creativity and positive thinking. If you’re looking for inspiration in your career or business ventures, I share a few examples below, to get you started!

The Importance of the Right Community

The right kind of community all depends on your needs and your personality. But basically it’s as simple as understanding who you connect with best. So what type of community is right for you? Ask yourself these questions:

Do you relate to artist-type freelancers more than the business-minded ones? That’s one of the great things about the Freelancers Union. They have a large network of sole-proprietors and freelancers who you can relate to, and tons of resources to help answer your questions.

Do you need help with your finances but are too intimidated to ask a professional? Try the ReadyForZero community, that helped me pay off over $14,000 of debt in 14 months. When you want to give up, everyone else who’s paying off debt and changing their money-mindset will help motivate you.

Do you want to be more balanced in life and work? Surround yourself with people who aren’t workaholics and who understand that it’s good to take time off for yourself. Read a few books, from authors like Danielle LaPorte or Gabby Bernstein, who focus on your well-being, not just the bottom line.

Reach Your Goals and Dreams Faster

Your friends and supporters are a powerful factor in the way you live your life, build your business and handle your finances. I’ve been lucky enough to connect with the right kind of communities that allowed me to reach my goals.

With their support (and constant reminder of why I was doing it), I was able to pay off my debt 7 months sooner than I originally anticipated. Yes, I still had to put in the work, but they were a sounding board, offering unique ideas, and were there when I needed a pick-me-up.

This gave me the motivation to stay with it, and once that ball was rolling, the momentum kept going until I finally reached my goal.