Freelancing Toward Financial Freedom


Have you ever thought, “I hate this job, but it pays the bills?”

I know I have.

But what other choice is there?  We all need to make money.

In late October, I decided to test the waters as a freelance writer and editor.  It had been nearly three months since I left my cushy, low six-figure corporate job and I was ready for a new challenge.

I had no idea where to start.  On a Facebook forum, somebody mentioned Flex Jobs as a good place to look for flexible, non-traditional work.  From there, I began exploring other freelance job platforms like Upwork and Freelance Writing Jobs.

Immediately, one thing stood out.  There is no shortage of people seeking freelancers to perform contract work.

With this preliminary research out of the way, I decided to jump in head first and go for it.

What did I have to lose?  After all, my wife’s job already covered our expenses and anything extra I made would be padding our savings and investment portfolio, paving the way toward financial freedom.

As I began getting clients and completing projects, it seemed selfish to keep these newfound insights to myself.  I needed to share this information to help others ditch the daily grind and build a career on their own terms.

So here I am, just a regular guy with no special skills, aside from an opportunistic nature and a penchant for taking calculated risks, going off on my own.  Do I have what it takes to grow a freelancing business from scratch and earn a decent living through flexible, yet unpredictable, work?

Let’s find out.

Over the next year, I will document this entire process right here.  Specifically, I will:

  • Try out various freelance job platforms
  • Track my monthly income
  • Report lessons learned and other helpful tips

My goal for 2017 is to earn an average of $3,500/month through freelance and other part-time work.  This will include income earned from my Air Force Reserve job, which, in my mind, perfectly complements this freelancing lifestyle.

To give you a baseline, in the last six weeks since I began freelancing I have earned $454.  Through November, I have made $15,626 as a reservist.  This makes my combined monthly average $1,462.

As you can see, I’ve got my work cut out for me!  While my reserve pay has been fairly regular and predictable over the last two years, I’ve only just begun freelancing and have no idea where it’ll take me.  After spending my entire career working for someone else, I’m entering uncharted territory.

For anyone looking to build a non-traditional career or simply make a little extra money on the side, I hope you will find this to be an interesting and useful experiment.

I want to leave you today with three tips I’ve already learned in my short time as a freelancer.

1. However long you think it’ll take to complete a project, double it.  In the beginning you’ll suck at estimating the time needed to finish a task.  Hint, you’re slower than you think.

2. Quickly identify clients you do not want to work with and avoid them.  After just a couple interactions, you can usually tell if someone will be a pain to work with.  They aren’t worth the hassle, other work is available.

3. If you’re not willing to work hard, don’t become a freelancer.  I’m working harder than I ever have before, but it has been much more satisfying.  Over time, I’m hoping the financial rewards will catch up to this sense of accomplishment.

*There are no affiliate links in this post.

19 thoughts on “Freelancing Toward Financial Freedom

  1. Maggie says:

    Obviously you’re doing this all for me and I’m thrilled about it! 🙂 I really want to dabble in freelance writing in 2017 but am struggling figuring out how to not take on too much. My real job is often slow, but can pick up quickly, so I will follow your lead! 🙂

    Liked by 2 people

    • Ditching the Grind says:

      Well, now the pressure is on!

      From what I’ve experienced so far, I don’t think you would need to worry about taking on too much work, at least not initially. This gives you some time to test out working with multiple clients and different types of writing assignments.

      I think you just have to go for it! In the meantime, I’ll continue to share any tips I think might be useful.


  2. Mrs. Mother Dirt says:

    I love that you will be sharing your experience. I am glad you brought up the time factor. I am curious how many hours you will actually be working. Good Luck!


    • Ditching the Grind says:

      Time is an interesting topic that I’ll talk more about another time. The week of Thanksgiving, I felt super busy because I needed to finish a couple articles and they took a lot longer than I expected. Other days, I don’t work at all and focus on personal stuff.

      Liked by 1 person

  3. chiefmomofficer says:

    Best of luck to you! I’ll be interested in seeing how freelancing works out. I’d love to do some on the side but right now I’m focusing on improving my writing and my content, and getting my message out into the world. Maybe someday!


    • Ditching the Grind says:

      Thanks! One thing that has taken a while is that I’ve really needed to take a step back and think about my personal brand, separate from this site, and what I wanted to focus on for freelancing. That was actually tougher than it sounds.

      Once you do decide to take the plunge, just go for it! Try writing for different types of clients and see what you like. Even now, you can scan boards just to see the types of freelance gigs that are out there.

      Liked by 1 person

  4. Graham @ Reverse The Crush says:

    This is a totally epic! Post! $454 is a nice chunk of extra money in only 6 weeks. Im still settling into the new role, but this is definitely motivating me to get started with Upwork.
    I’m looking forward to reading about your freelance progress over the next year. Good luck on the income goals and thanks for sharing the freelance tips.


    • Ditching the Grind says:

      Thanks, Graham! Actually, the vast majority has been made during the last 3 weeks. We had family in town so I didn’t do anything the first two weeks of November.

      I’m glad your new role is going well. Hope it turns out to be a good fit!


  5. Vladimir Covic says:

    Thanks for posting this! I’d also add to new freelancers to be prepared for late and non-payments all the time. You never know what’s going to happen, but you have to still have to pay your bills.


    • Ditching the Grind says:

      You’re welcome and great point. I’ve already noticed a little bit of this myself. It took just over a week for a client to approve work I sent them. Then, depending on the platform used to get the work, it could be several more weeks until payment is received. This isn’t a big deal for me, but people need to be aware that payment likely won’t be immediate.


  6. Rhonda says:

    Nice post. Definitely true perspective. I’ve been freelancing since 2013. Though my efforts were more defined by 2014 so I really feel I’ve been a true freelancer for 3 years. Their are lots of pros and cons. Just wait until you get the “expletive” guy who tells you he can hire a good Indian for $5.00 an hour. In no way am I disparaging workers from India when I say that. Indeed, I am in support solely of the American worker because that is the focus of my ow blog and in my own life as a freelancer. My point is, there are guys hiring freelancers who feel they can bully you into lower rates. You have to stand your ground and walk away. For someone in India, maybe $2, $3, or $5/hourly is good pay. Maybe $500 a month works for the guy who lives there. However, It’s not feasible to expect an American freelancer to work at such a rate. On the opposite end, I have a long-term client who has really only ever hired low-wage foreign workers. It took time to show him the value of why he was paying me over a much lower wage. We have been working together for over 1 year now and my wage is decent. Proof that your point 2 and 3 have good merit. Good luck, keep at it. I almost quit because it seemed impossible. However it is worth it

    Liked by 1 person

    • Ditching the Grind says:

      Rhonda, thanks for sharing your perspective as a more experienced freelancer. I’ve definitely noticed certain jobs and clients that seem to focus on the foreign workers that are willing to accept pay like you described above. I’ve been avoiding those jobs.

      Thankfully everyone I’ve interacted with so far has been courteous and professional, so no expletive guy… yet.

      I’m working with a client now that seems to have good mid to long term potential and I hope it works out. Solid pay and interesting work.

      Best of luck to you as well!

      Liked by 1 person

  7. helencoxmarketing says:

    I’ve just taken to plunger too and left a well paying job for the freedom of freelancing. The corporate 9-5 is just not for me anymore!

    I completely agree with knowing who you dont’ want to work with – you learn pretty fast who they are and I say go with gut instinct! If you’re not sure you want to work with them don’t!

    Liked by 1 person

    • Ditching the Grind says:

      Like you, I just can’t see myself going back to the 9-5. Clients who will be a pain seem to show their colors pretty quickly from what I’ve seen so far. The gut instinct is definitely a good indicator.

      Best of luck with luck with your freelance business, Helen!

      Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s