6 Lessons I Learned in My First 6 Months of Being Self-Employed

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self-employment lessons learned

This post is from Careful Cents contributor Erin, who owns the blog Journey to Saving. Over a period of six months she documented her backwards journey to self-employment. You can read what she’s learned here.

Over the past six months, I’ve had the privilege of being able to share my journey of my backwards approach to becoming a full-time freelancer with all of you, and now I’m here to wrap up the important lessons I’ve learned in that time.

I’ve been sharing quite a few of them with you along the way, and I hope my insight has helped you along your journey to making the switch from the 9-5 into self-employment.

If you’re thinking about jumping headfirst into being a freelancer, or you’re at the beginning stages, here are the biggest lessons and takeaways from my journey.

Lessons #1: Embrace experimenting

Originally, I started out as a freelance writer, simply because I had already been blogging, and it made sense at the time.

However, after several months of writing, I felt myself burning out. After talking with a few other freelance writers, I discovered I wasn’t alone. When I found out others, that I looked up to, were also struggling and trying to branch out, it gave me the courage to diversify my work.

I decided I wanted to be a virtual assistant, so I started offering services outside of writing. Being a VA means wearing a bunch of hats on a daily basis, and it’s been a huge learning experience.

I wouldn’t recommend being so diversified you drive yourself nuts with all the different tasks you have to complete, but don’t be afraid to try something new if what you’re doing now isn’t working or doesn’t feel right.

Maybe you already know your purpose and calling, but a lot of freelancers start out with a few small ideas and figure it out along the way. That’s okay. Things tend to work themselves out!

We’re all on the same type of journey — to figure out where we ultimately want ourselves and our businesses to end up. We’re always evolving, and our business and our interests must evolve, too.

That’s why I think it’s awesome Carrie is focusing on her business this year. I think that’s a goal many of us are working toward.

Lesson #2: Be patient and have faith

Some of us must work our way up to focusing on our own businesses slowly because we need a more immediate source of income. The reality is, when you start from nothing, you can’t expect to be an overnight sensation. It takes time to build your portfolio, to get comfortable with marketing, and to grow your network.

Those that side hustle have an advantage as they can (hopefully) make the leap and have all of this in place. I didn’t have this opportunity before I quit my job. I did it a bit backwards.

The one pitfall I have to warn you about here is to make sure you can properly handle periods of rejection, hearing nothing back, and making (what seems like) little-to-no progress.

When I was around month 3 of being my own boss, it felt like I hit a wall. I had friends assuring me that it can take up to 6 months to really hit your stride, and they were absolutely right.

If you feel like you’re in a lull now, have faith that if you continue to be persistent, you’ll find work. Whether you make your own opportunities or they come to you via your network or marketing tactics, there are more than enough jobs to go around.

Lesson #3: Avoid perfectionism

As a perfectionist, I don’t say this lightly, but it’s true. Your desire to have everything turn out perfectly will hold you back, just as much as fear will.

There have been many pieces I’ve written that I haven’t been 100% happy with, but what am I going to do? Re-read it and re-write it 10 times? Chances are, your energy is best spent elsewhere — not on something that is (likely) a finished product.

We all judge our own work more harshly than the work of others. If you’re having serious doubts about your work, get the opinion of a close friend, accountability partner, family member, or colleague.

You need to know when to let go and move on to the next thing, especially when you have limited amounts of time (and let’s face it, we could all use more!).

Lesson #4: Don’t undervalue yourself

I know pricing can be tricky to tackle, especially when you’re brand new. Don’t be afraid to ask others what they charge to get a feel of what average rates are. (Of course, you should also know how much you need to earn to make a living!)

Just because you’re a “beginner” doesn’t mean you have to charge the lowest rates possible. Charge what you’re worth. Remember, if you price yourself too low, then prospective clients are going to wonder if you’re bringing any value to the table.

One of your jobs as a freelancer is to make price a non-issue. Find a way to show, and prove, how much you’re worth. Focus on offering solutions that people need.

Also, don’t be afraid to ask for a raise. The more time you spend working with a client, the more valuable you become. If your clients are happy with your work, and you make their lives easier, then they will want to continue working with you.

Lastly, aim for clients that can afford you. This is the best tip I can give you as far as pricing! Stop wishing that clients pay you more money, and start finding the ones that are more than willing to see your value.

If you’re a freelance writer, blogging on behalf of a corporate entity is going to pay more than being a staff writer on a smaller blog. Go for the clients with bigger budgets who don’t mind paying for quality.

Lesson #5: Push past fear and just start

I know I’ve said this one before, but it absolutely bears repeating. I was stuck for so many months because I was afraid to put myself and my work out there. As creatives, we become very attached to and protective of our work. It can hurt to hear criticism sometimes, and we tend to withdraw and hide our masterpieces away in the shadows where no one can find them.

But that’s not going to get us anywhere. It’s better to make something, even if it ends up being embarrassing years later, than to sell out on your creativity. We all start somewhere, and we must go through this process to become better.

Think of it this way: whenever you write a post, whenever you draw an image, whenever you paint a scene from your mind, you’re creating something from nothing. You’re giving life to your ideas, and your ideas have the ability to inspire others.

That isn’t something you should keep under lock and key. I guarantee you that someone out there will appreciate your work. Just start.

Lesson #6: Trust yourself and others

Even though being a backwards freelancer has been extremely challenging, I would do it again in a heartbeat.

I learned so much about my strengths, my weaknesses, and my resolve through building a business this way. That knowledge is invaluable, and I know that if I ever return to the “traditional workforce,” I have more value to bring than I did before.

As for what I would do differently, I wouldn’t be afraid of investing in myself and I’d hire a business coach right off the bat to help me get started. No chance of procrastinating that way.

I’d ask for advice from others sooner. Learning from others is something we should all make a habit of.

Lastly, I’d build up my support network more. Starting my freelance journey after moving to a new area made things more challenging, as I didn’t know anyone here. Don’t isolate yourself!

Thank you for reading and being a part of this journey with me. I hope I’ve been able to inspire some of you to take the leap, and please know that if you ever need words of encouragement or advice, leave a comment and I’ll respond.


  1. I’m at the same point as you and have just made it to the six month mark. I started out with the sideways shuffle though, working part-time to stay afloat and then moved full-time freelancer after I gained confidence at around 2 months of work.

    It’s all of juggling game of finding the right clients for the skills you can offer but so far, so good. Your tips in this article are great – gave me new enthusiasm to keep on going on the freelance road!

    • Erin says:

      Congrats on also making it to the 6 month mark! It’s great you were able to make the leap after 2 months – I hope you’ve been enjoying it. =) Glad you liked my tips!

  2. Tammy F. says:

    Always refreshing to hear a success story for those that know what they have & put it to work. You did not let others stand in your way of success to achieve the talents, gifts, tools, skills etc & put them to work for you. You did it your way not always the easy way but the right way. Congratulations on your success & all the best wishes & good luck for all your future endeavors

    • Jeanne W says:

      I am so ready to get started. I’m ecstatic to have found your story.you have inspired me to get over my fears & take the plunge.Wish me luck & good fortune, cuz world here I come!

      • Erin says:

        Jeanne, that means so much to me! I’m super excited to hear that, and if you have any questions, feel free to reach out. Best of luck!

    • Erin says:

      Thank you so much for your kind words, Tammy! I’m still in a bit of disbelief I was able to make it work, but I’m so grateful for the amazing people that joined me on my journey and helped me out. It was definitely not a solo effort, and I wouldn’t have had it any other way.

  3. Marie says:

    Congrats for sticking with it and seeing your hard work pay off! I too went into this full-time freelance thing without fully planning ahead, and then my main client disappeared and I’ve been running around like a chicken with my head cut off. I will take faith from your post!

  4. I’ve literally just embarked on my freelance writing journey so this post was perfect to read. I plan to start off as a side hustle but want to be able to make the leap by July. I’ve recently had a couple of guest blog posts accepted and published so I want to use this confidence to move forward. Thanks for sharing your story. 🙂

  5. Celise says:

    That’s why I’ve decided not to be a freelance writer. I write as a hobby and enjoy it and I’ve always thought that writing to bring in extra income would make my hobby writing seem like “work” writing. HOWEVER, I love to read and have decided to try my hand at editing fiction novels (I’ve signed up for a course that starts June 1st) and then eventually offering copyediting services.

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