• Skip to primary navigation
  • Skip to main content
Collective

Collective

A blog to help freelancers with taxes - Collective

What we offer

Business setup Form your business the right way Accounting Expert approved, powered by AI Invoicing Get paid faster, without the busywork Payroll Payroll made simple for S Corps Taxes Stress-free taxes for solopreneurs Business insurance Coverage for your business Health insurance Instant and affordable health coverage Support Human expertise + AI speed
Pricing Customers
About us Partnerships Careers We're hiring! Press
Blog Newsletter Webinars

Free tools

S Corp tax savings calculator Estimated tax & extension calculator Tax calendar S Corp admin cost calculator Freelance rate calculator Bill rate calculator
See all free tools →
Login
Business setup Accounting Invoicing Payroll Taxes Business insurance Health insurance Support
Pricing
Customers
About us Partnerships Careers We're hiring! Press
Blog Newsletter Webinars S Corp tax savings calculator Estimated tax & extension calculator Tax calendar S Corp admin cost calculator Freelance rate calculator Bill rate calculator See all free tools
Login
Resources / Small Business Hacks · 6 min read

How to embrace an ROI mindset and grow your self-employed business

Learn how to adopt an ROI mindset to effectively scale and grow your self-employed business for long-term success.

Woman leaning on desk with arms crossed. Wearing a white blouse
Morgan Overholt
Written by Morgan Overholt
Eric Poole
Updated by Eric Poole
Published Mar 11, 2021 · Last updated Jul 10, 2024
On this page 4 sections
  1. What’s ROI?
  2. Do you have to spend money to make money as a freelancer?
  3. So how much time and money should you spend? 
  4. Ignoring the naysayers

AI Summary

AI-generated from this article. Not tax advice.

  • The author frames a $10 Upwork gig — which netted $8 after commission but earned her first 5-star review — as a marketing investment that made landing future, better-paid work easier.
  • Return on investment gauges profitability relative to cost and can apply to gains in opportunity and growth, not just money and profit margins.
  • She contrasts good ROI with a conference that cost about $1,500 and a week of her time but produced no new contracts or leads.
  • She argues freelancers probably do have to spend money to make money, but strategically, choosing the option with the better ROI, and estimates she has paid about $40,000 to Upwork against roughly $400,000 earned.

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, username.wixsite.com/siteaddress). 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. 

Get help with your freelancer needs

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. 

Our website contains general information only and this information is not to be taken as legal, tax, or financial advice. You should consult with your attorney and/or tax advisor to get answers to your specific questions.

Get help with your freelancer needs

Collective handles the tax and accounting side of your business – so you have more time to focus on your passion. LLC formation, S Corp election, bookkeeping, monthly financial reporting and an average member tax savings of $10,000*.

Get Started

More on Small Business Hacks

All Small Business Hacks posts
Blog

Unlocking the Zone of Genius: What the Right Support Actually Looks Like for Solopreneurs

Running a business alone means wearing every hat, all the time. The invoicing hat,…

Aug 10, 2026 · 4 min read
Blog

The S Corp Owner’s Mid-Year Check-In: Is Your Structure Doing What It Should?

If you’re running your business under an S Corp election, mid-year is a worthwhile…

Jun 11, 2026 · 5 min read
Blog

The Sole Proprietor’s Mid-Year Check-In: Is Your Setup Still Working for You?

Most people who start working for themselves don’t sit down and choose a business…

Jun 11, 2026 · 6 min read
Blog

Self-Employed Retirement Plan Limits Just Changed for 2026: Here’s What’s New

The IRS adjusts retirement plan contribution limits most years, and 2026 brings increases across…

Jun 10, 2026 · 7 min read
Blog

Self-Employed Retirement Plans: 2025 Contribution Limits and Your Best Options

When you work for yourself, no one is automatically setting aside money for your…

Jun 10, 2026 · 4 min read
Blog

Your LLC Turns One. Here’s What to Do Next.

One year in means something. You have real income, real expenses, and at least…

May 20, 2026 · 6 min read
Blog

Business Expenses for Social Media Influencers

We LOVE our members that are crushing it as social media influencers. One common…

Dec 10, 2024 · 5 min read
Blog

Meal and Entertainment Deductions

Business meals are a common expense, but what is tax deductible can be tricky…

Dec 10, 2024 · 3 min read
Blog

Differences Between Employee and Independent Contractor

If you’re a business owner, you’ll likely come to a point where you need…

Mar 20, 2024 · 6 min read
Blog

Should I Hire a 1099 Contractor or W-2 Employee?

As your business expands, you might need more help than your current capacity allows.…

Mar 13, 2024 · 6 min read
Blog

 How to Build Business Credit

Most people are familiar with the concept of credit scores. Major credit bureaus track…

Mar 4, 2024 · 5 min read
Blog

How To Handle Business Inventory

If your business carries inventory, effective inventory management is critical. Whether you’re running a…

Feb 20, 2024 · 7 min read
Blog

How to Take Parental Leave When You’re Self-Employed

Welcoming a new baby can be both exciting and stressful. On top of caring…

Nov 6, 2023 · 5 min read
Blog

The 6 Lead Generation Mistakes to Avoid In Your Solo Consulting Business

This blog is written by guest author Melisa Liberman. Melisa has been an independent…

Oct 4, 2022 · 10 min read
Blog

How To Establish An Effective Lead Generation Routine As An Independent Consultant – A Case Study

It’s common for independent consultants to miss an important step when designing their lead…

Jun 8, 2022 · 9 min read
Blog

Tips for Creatives to Overcome Isolation and Loneliness

Being a Business-of-One has plenty of perks (hello having full control over when you…

Dec 8, 2021 · 4 min read
Blog

How to Turn a Referral Program Into a Main Source of Income

When I discovered Collective almost three years ago, I had little idea of what…

Nov 10, 2021 · 5 min read
Small Business Hacks

How to improve your payments workflow

As a creator, doing the work is often the easy part. Getting paid? Well,…

Sep 29, 2021 · 4 min read
Small Business Hacks

Want a sustainable business? Try diversifying your income

I’m sure you’ve heard that the average millionaire has 7 streams of income. I…

Sep 9, 2021 · 5 min read
Blog

7 Tips for Successfully Hiring Your First Freelancer

Learning how to find and hire the right help to scale my business has…

Aug 27, 2021 · 9 min read

About the author

Morgan Overholt

Morgan Overholt

Tennessee native Morgan Overholt is a graphic designer with nearly 20 years of experience and the owner of Morgan Media LLC, a design and marketing agency she launched in 2017 after a decade in corporate roles. She and her team have worked with clients including the Centers for Disease Control Foundation, Kimberly-Clark, and Stanley Black & Decker. Morgan is a regular contributor to Business Insider and has also been featured on Upwork and Refinery29, and previously co-founded TheSmokies.com. For Collective, she writes from firsthand experience on the realities of freelance life — from setting rates and hiring help to scaling a business and navigating difficult clients.

All articles by Morgan

Best for S Corp owners

Payroll, books and filings in one membership

LLC Tier $199/mo · S Corp Tier $349/mo

Related

  • Unlocking the Zone of Genius: What the Right Support Actually Looks Like for Solopreneurs
  • The S Corp Owner’s Mid-Year Check-In: Is Your Structure Doing What It Should?
  • The Sole Proprietor’s Mid-Year Check-In: Is Your Setup Still Working for You?

Latest

  • A New Era of Entrepreneurship
  • Collective Raises $100M for Full Stack AI Financial OS Powering the Solopreneur Revolution
  • The Vampire Expenses Draining Your Business

We’re glad you’re here!

First, tell us about your business

Net profit = Total revenue - total expenses

  1. Find total revenue. Add up all money your business earned from sales of goods or services during the year.
  2. Subtract your expenses. Deduct all business costs like supplies, rent, utilities, software, contractor payments, and loan interest.

An estimate is fine, you don't need exact figures.

W2 employees are people on your payroll

You withhold income tax, Social Security, and Medicare from their paychecks, and they get a W-2 form from you at the end of the year.

Don't count yourself (even if you pay yourself a salary) or 1099 contractors and freelancers.

I agree to Collective Terms of Service & Privacy Policy. Additionally, by providing phone number to continue, I agree to receive calls, incl. autodialed or prerecorded sales calls, from Collective.

Collective logo

We are experts in the unique needs and challenges of self-employed people and know that our confidence gives others confidence, too. Reach out to say hello and join our team.

We are experts in the unique needs and challenges of self-employed people and know that our confidence gives others confidence, too. Reach out to say hello and join our team.

Products

  • Business setup
  • Accounting
  • Invoicing
  • Payroll
  • Taxes
  • Business insurance
  • Health insurance
  • Support
  • Late S Corp election

Company

  • Home
  • Pricing
  • About us
  • Careers
  • Contact us
  • Partnerships

Resources

  • Blog
  • Guides
  • Help center
  • Testimonials
  • Press
  • Create with us

Legal/Support

  • FAQ
  • Terms of service
  • Privacy policy
  • Security policy

Compare

  • Compare all
  • Collective vs Lettuce
  • Collective vs LegalZoom
  • Collective vs TurboTax
  • Collective vs ZenBusiness

Collective provides a suite of tools, back-office support, and general information. Our services are not intended as tax, legal, or professional advice.

* Savings estimates reflect the average 2023 federal self-employment (SE) tax savings for Collective members with an S Corp tax election, based on business profits that would've otherwise been subject to SE tax. Actual savings will vary based on individual circumstances.

** Based on data sourced from Shopify blog, QBO Essentials, QBO Live, Gusto, Taxfyle, Intuit "Tax Pro" Research, LegalZoom and JustAnswer.com as of August 2025.

† Individual tax return packages are billed as an annual, one-time add-on fee.

© 2026 Collective Hub, Inc. All rights reserved