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Spending money to make money: A guide to ROI

I remember having a conversation with my husband about taking on a $10 gig on Upwork, a freelancer marketplace, shortly after quitting my job to become a full-time freelancer.

I worried I was selling myself short, despite the fact that the job was small and could be completed in well under an hour.

Not to mention the fact that the $10 would actually turn into $8 after Upwork’s 20% commission.

My husband, in his infinite wisdom, simply said, “Consider it a marketing expense. If that $10 job lands you a review that helps you land more work or better jobs in the future, it’s worth its weight in gold.”

He was right. Fast forward three years later, and I’ve made more than $400,000 on Upwork alone. I currently land jobs at $120 per hour on the platform.

I can’t help but wonder how my career would have turned out had I let my ego get the best of me and turned down that small opportunity. That $10 job did more than just help me land future work. It also taught me about the importance of ROI.

What’s ROI?

Return on investment (ROI) is a performance metric used to gauge the profitability of an investment relative to its cost.

While ROI traditionally refers to money and profit margins, it can also refer to gains in other areas, like opportunity or growth.

To use my earlier example, the cost of taking that job was 30 minutes plus a $2 fee. The return on that investment was an $8 profit and my first 5-star Upwork review, which made it substantially easier for me to land my next project.

By comparison, the other things I was trying at the time to find freelance work simply weren’t producing a meaningful ROI.

That same year, I attended the National Conference on Health Communication, Marketing and Media on the advice of one of my clients. Between tickets, gas and the hotel, I ended up spending about $1500 and about a week of my time. Despite my best networking efforts, at the end of the week I landed no new contracts and no promising leads. That’s an example of a poor ROI.

Do you have to spend money to make money as a freelancer?

Which brings us to a very important question: As a freelancer, do you have to spend money to make money?

And the answer to that question is the same answer I would offer to any small business owner: Probably.

But you’ll need to do so strategically.

If you’re treating your freelance career like a small business, and I hope you are, you already know there are going to be some costs involved.

For instance, you will likely need the basics: An internet connection, a computer, a desk and a chair. There are costs associated with each of these items. No one ever said freelancing would be free.

Then you have marketing expenses such as a website, ads, networking events and social media.

The cost of these items may vary greatly depending on your particular needs and the efficiency of your strategies.

For instance, you can build your own portfolio website using a free website builder like Wix and use the long, free URL (for example, It’s still going to require a considerable amount of time and effort, but it will help keep your monetary costs low.

Others may opt for a more professional, ad-free look and short domain names, all of which will take more time and more money.

But which route should you take as a freelancer? Once again, the answer is the one that provides the better ROI.

If you’re able to win better projects because of a professional looking website, then spending a little more time and money is likely a better overall investment.

On the flip side, if having a great website doesn’t affect your earnings or ability to win jobs, it’s probably not worth the investment.

There’s also the matter of whether or not you have money or time to spend in the first place.

Not everyone has a lot of funds starting out. And that’s okay too. Just know that everything is about scale. Do what you can in the beginning.

We all had to start somewhere. My freelance business today barely resembles my freshly launched business in early 2017.

With each small gain, put a little bit back into the business. It becomes easier to invest in yourself and scale your business as you grow.

So how much time and money should you spend?

As a fan of Shark Tank, I always have the voice of “Mr. Wonderful” Kevin O’Leary in the back of my head.

“Here’s how I think of my money — as soldiers,” O’Leary often says on the show. “I send them out to war every day. I want them to take prisoners and come home so there’s more of them.”

There is no magic formula or single right answer for everyone in every business. However, it’s important to constantly experiment with growth strategies.

Like O’Leary’s soldiers, you may suffer a few casualties along the way because it’s unlikely that you’ll get it right the first time, every time.

But inevitably your soldiers will begin to multiply. That’s when you know you’re onto something worth chasing.

By using this ROI mindset in my own business, I’ve been able to transform my annual revenue from $40,000 in that first year to almost $300,000 per year and growing.

I’ve accomplished this through blogging, hiring help, creating multiple revenue streams and never shying away from things just because they seem hard or require spending a little money.

Ignoring the naysayers

Finally, the biggest thing to keep in mind when it comes to running and scaling your business is the importance of ignoring the naysayers, whose primary objections often seem to revolve around money.

Most commonly, at least for me, the objections are usually about either Upwork fees or health insurance.

There’s even an entire blog post about me from three years ago on Hacker Noon that talks about how I had to pay “at least $10K in Upwork fees” and how he feels “sorry” for my clients.

While I do pay roughly 7% commission to Upwork for jobs I obtain through the platform (a drop from 20% due to my high volume of work), I also get the benefit of using them as the middleman for contracts, invoicing and client acquisition.

In fact I roughly estimate that I’ve paid about $40,000 to Upwork in total at the time of this writing.

But if I told you that you could give me $40,000 in exchange for $400,000 — wouldn’t you take it?

That’s a 90% profit margin. What do you think Mr. Wonderful would have to say about that return on investment?

The same thing goes for my health insurance.

I do have to pay for private health insurance, and yes, it is more expensive than traditional corporate policies.

But why would I want to go back to making $75,000 per year as a salaried employee just to save a couple hundred dollars a month on insurance premiums?

Never worry about saving a penny if it prevents you from making a dollar.

At the end of the day, adopting an ROI mindset might just be the best thing you could do for yourself and your business.

Tennessee native Morgan Overholt is a freelance graphic designer, owner of Morgan Media LLC and co-founder of Morgan and her team have worked with nationally recognized clientele from all over the world, including the Centers for Disease Control Foundation (CDCF), Kimberly-Clark, and Stanley Black & Decker.

Morgan transitioned into the role of freelancer and small business owner after spending nearly a decade in the traditional corporate world left her feeling unsatisfied and unfulfilled. Today, Morgan is passionate about sharing her story with other hopeful entrepreneurs who hope to follow in her footsteps. She has been featured on, Refinery29, and Business Insider.Originally published at on March 12, 2021.



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Morgan Overholt

Morgan Overholt is a freelance graphic designer and owner of Morgan Media LLC. She is also a contributor for Business Insider and Collective.