My Freelancing Strategy


Although I didn’t know the term existed until the last year or so, I’m realizing that I always wanted to be a solopreneur.  The traditional 9-5 grind was never for me.  For years I’ve had tons of business ideas and, when I think back to them, they were always solo gigs.

I never wanted to grow a massive company.  Instead, I wanted to help people, mostly small businesses with limited resources, reach their goals.

My aim has never been to become super rich, I just want to be comfortable… actually, being super rich would be pretty cool.  Can’t say I’ve never thought about that!

Even more though, I wanted freedom.  The freedom to do anything I wanted on any given day, to work as much or as little as I desired, or pursue completely separate interests altogether.

Isn’t that what everyone wants?

I guess this is where it all ties back to financial independence.  Once you’ve built sufficient “F-You” money, you no longer need to suck up to a boss and are more free to take career risks.

And speaking of careers, it finally feels like I’m on the right path.  Even though I’m not making much right now, I’m actually having fun working.

I really want to stick with it, too, because if I can fulfill the vision of where I see this going, the financial rewards will come.  So why am I telling you all this?  Three reasons: it helps me clarify my thoughts, I want to be held accountable, and I hope to possibly inspire others to follow their own dreams of ditching the daily grind.

A Phased Approach to Building a Freelance Career

Short Term –Experimenting and Learning (4-6 months)

This is where I’m at right now.  I have no idea what I’m doing and I’m just winging it.  There’s so much I don’t know and every day I’m learning more.  I’m taking on different types of work and figuring out what I’m good at and what I enjoy.  I’m intentionally taking on some work with fairly low pay because it’s building skills that I know I’ll need down the road.

My current work is mostly transactional and project-based.  Utilizing freelance platforms with built-in payment systems, like Upwork, allows me to focus on client interactions and producing quality work without worrying about how to accept money and find clients on my own.

Mid Term – Focus on a Specific Niche (6-12 months)

Eventually, though, as I learn my strengths and concentrate on a specific niche, I’ll also want to cut out the middleman and begin acquiring clients directly.  At the same time, the work I’m doing should become less transactional, more relationship-based… and hopefully higher paying!

This also means I’ll need to be a real business with an invoice and payment acceptance system.  To keep my freelancing and personal finances separate, I’ll be setting up an LLC before entering this phase (I should really start doing this now).

Long Term – Focused Niche with Steady Stream of Clients (1 year and beyond)

By the end of 2017, I’m hoping to have a pretty decent little business going.  This is not meant to become a regular 40+ hours a week gig, though it may be in spurts.  I’m looking to build flexible and enjoyable work to act as supplemental income for our family and help me continue to grow as a person.

In my last post, I said my goal for 2017 was to make $3,500/month between this and my Air Force Reserve job.  I don’t think this will happen immediately.  Early months will likely be closer to $1,500-2,000, potentially ramping up to around $5,000 by the end of the year.

At that point, I’m hoping that most of my clients will be found independently from freelance platforms where I have to pay a commission on each job, but who knows how it’ll actually play out.

Regardless, I’m excited to see where this takes me.  I may crash and burn, an utter failure, or I may succeed beyond imagination.  Let’s find out!

Obviously, this is just an outline of my big-picture strategy.  Lots of little details still need to be worked out.  Is there anything else I should consider moving forward?

7 thoughts on “My Freelancing Strategy

  1. Graham @ Reverse The Crush says:

    Great read DTG!
    I’m really enjoying your freelance updates. It makes me think I should’ve pursued it more while I was off. Hopefully I can learn from your experience.

    Also, you really are my like my blogging alter ego…

    “I never wanted to grow a massive company. Instead, I wanted to help people, mostly small businesses with limited resources, reach their goals.

    My aim has never been to become super rich, I just want to be comfortable… actually, being super rich would be pretty cool. Can’t say I’ve never thought about that!”

    I feel the same…

    I’m also inspired by your adherence to the new posting schedule. I’m readjusting to the grind but I want to establish a schedule eventually too. Keep it up man!


    • Ditching the Grind says:

      Thanks, like I said above, I’m just winging it and seeing what happens. Honestly, part of what is driving me is that I don’t want my wife to be the only one bringing in some money. I feel better when I’m at least contributing a little bit. We have a nice stockpile, but still.

      The posting schedule has been good for me. Because I made a public announcement, I feel obligated to post and it actually makes me plan ahead for content. Readership is trending upwards, too, which is as added bonus.


  2. Maggie says:

    I like your strategy. I also agree that having a large business sounds stressful (that’s not what you said? Oh. That’s what I heard! 🙂 ) – A small, income-generating side plan is perfect. My freelance plan for next year: send out 2-3 pitches a month and then reach a certain level of income per freelance article by the end of the year. It’s simple, but we’ll see if it works. 🙂


  3. Vladimir Covic says:

    Thank you for this post DTG. I look forward to seeing how it worked out for you (hopefully well). Of course, you have to keep in mind that it might take longer than what you expect.


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