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5 Tips on How to Scale a Business from a Successful Freelancer

In the early stages of my business, my main goal was to generate enough revenue to provide for myself and my family. Sustainability was my focus, and scaling my business was the furthest thing from my mind.

But in just eight months, I found myself at an unexpected crossroads. I had more work than I could handle on my own and knew I needed to hire help to keep up with demand.

Today, my business has scaled into multiple ventures including a small freelance design agency, two blogs and a small co-lab with a combined annual revenue of about $350,000 per year and growing.

From my first freelance hire to adding additional revenue streams to my portfolio, learning how to scale a small business has been both one of the most challenging and most rewarding aspects of my career.

Here are the lessons I’ve learned about how to scale a business along the way.

Scale your business incrementally, learn from your mistakes

There’s nothing wrong with dreaming big.

But as the old saying goes: “It’s best not to bite off more than you can chew.”

While I’ve enjoyed a lot of success, I’ve also made plenty of mistakes. And making too many mistakes at once, or too many mistakes early on, can be detrimental to a small business.

That’s why I’ve always focused more on how to meet the needs of the moment rather than trying to grow too big too soon. In other words, I focus on sustainable growth.

This also allows me to keep the overall risk/reward ratio stacked in my favor.

I only hire help when we have enough work to justify bringing extra team members onboard. And when adding a new potential revenue stream, I make sure it’s not at the expense of the already successful branches of the business.

For instance, when I bought commercial office space, I made sure it was an expense that could be easily absorbed instead of sinking the business if I wasn’t able to find renters (more on that later).

It’s also important to treat every mistake as a learning opportunity and adjust the strategy as needed.

Mistakes are inevitable , but if you let them make you stronger, you’ll be better off for it in the long run.

Build a network of talent that you can trust

As you scale your business , you’ll likely need to expand your team. But hiring the right people for the job can be a surprisingly difficult task.

As I scaled, I wanted to create a team of freelancers who both understood the industry and complemented each other’s talents.

I personally chose to stick with freelancers rather than traditional employees because they offer my business (and my bottom line) more flexibility.

Some weeks require all hands on deck. Some weeks, we only need a couple of people. Freelancers make it possible to scale up and down as needed.

I made it easy on myself in the beginning by dipping into my own personal network of talented and trusted individuals.

My first two hires were my younger sister and a friend from college. Each were talented artists and brought their own unique skill sets to the table, which also allowed us to expand our offerings.

However, my next few hires weren’t quite as seamless.

It turns out it’s much easier to hire your own friends and family than it is to hire strangers.

In fact, the process made me more appreciative of what clients must go through.

I experimented with traditional job sites like Indeed, online marketplaces like Upwork and even staffing agencies.I’ve also experimented with several hiring processes like lengthy Zoom interviews, informal calls and paid “trial” projects.

After a lot of trial and error, I’ve finally identified a winning formula when it comes to finding freelance talent for my team.

For me, it’s a combination of focusing my efforts on freelance marketplaces (Upwork is my favorite), vetting technical skills and establishing a mutual trust early in the engagement.

In my line of work, graphic design, the most common issue I encounter is a freelancer who seems confident but fails to deliver a quality product, or fails to deliver on time.

I’ve personally learned to compensate for this problem by keeping the interview phase brief, asking more technical questions upfront and assigning a smaller paid trial project before trusting a new hire with anything extremely important.

If I can’t come up with a bite-sized trial project, I pad the deadline by several days to give myself extra time in case I, or someone else on my team, needs to take over. I’ve had one too many sleepless nights redoing a project at the last minute because a freelancer failed to deliver.

And trust goes both ways.

It’s also important that the freelancer gets to know me and learns to trust that I’ll be the kind of client who strives to communicate effectively, has reasonable expectations and always pays on time.

This leads me to the third biggest lesson I’ve learned about how to scale a business.

Learn how to delegate and effectively utilize your team’s talent

One of the biggest lessons I’ve learned as a small business owner is how to utilize my team’s natural strengths and harness the power of delegation.

Early on, I thought I had to be a “jack of all trades” and expected my team to follow suit.

After a while, I realized that this mindset was a recipe for constant stress and would never allow anyone’s natural gifts and talents to shine.

In our everyday lives, we hire subject matter experts (SMEs) all the time.

When we have a cavity, we go to a dentist. When our car breaks down, we take it to a mechanic. When our taxes are complicated, we hire an accountant.

Imagine if we tried to become an expert in every facet of our day to day lives. It’s virtually impossible. There’s not enough time in the day.

Recognizing strengths and weaknesses within yourself and each of your team members is not only key to growing your businesses but will also improve overall team morale.

Several years ago, I asked my best cartoonist to design a logo. He seemed uneasy and uncertain about his ability to deliver, and not surprisingly, his final logo design wasn’t great.

And the disappointment was palpable. He felt he let me down. And I felt that I had let him down by setting him up for failure.

This doesn’t mean that he isn’t a talented cartoonist. In fact, he is one of the best I’ve ever met — I just wasn’t making a great use of his true talent.

Using the same example from above, I wouldn’t ask my dentist to fix my car, or my accountant to fill my cavity.

By cultivating a pool of experts in a variety of fields, I attract the best talent in each respective niche.

My team is happy because they get to do what they love, and my clients are happy because they are the beneficiary of a better product.

I’ve also become happier and less stressed as I learn to delegate the tasks that I don’t enjoy or can’t effectively perform — like letting the professionals at handle my taxes and bookkeeping, for instance.

Taking a step back and allowing other experts to step up has been key in my ability to scale over time.

Focus on long term relationships

One of the factors that I credit to my rapid growth as a freelancer is my focus on long-term professional relationships. And that goes for both my clients and my own team.

When finding new clients and new gigs, I actively seek out long-term contracts and ongoing work. I also try to treat my clients more like co-workers and team members rather than “employers”.

Seeking out long-term relationships with clients is beneficial in a variety of ways, including:

  1. More predictable (steady) income
  2. Less time spent on applying for new work and writing contracts
  3. Better client referrals

The highest-earning business owners in the world know that the name of the game is figuring out a way to spend more time earning and less time on paperwork, pitching and worrying about getting paid.

Long-term client relationships facilitate that goal.

I also focus on long-term freelancer relationships when it comes to my own network.

My top freelancer, my sister, has become my right hand (wo)man over the years and is in the trenches with me every single day.

Our best illustrator and best branding guru have both been working with us now for more than three years.

It’s this core group of talent who I know will always have my back, and continue to make me look great on a daily basis.

Create multiple streams of income

One of the things that I credit to keeping my small business afloat all these years — even through a global pandemic — is building multiple streams of income into my business model.

My personal monthly breakdown, lately, has looked something like this:

And even my freelance clientele is extremely diverse. My active clientele represent a variety of niches ranging from retail to health to government subcontractors.

That’s why my business was able to remain mostly unaffected during the shutdowns in spring of 2020.

Many of my retail clients were forced to halt or scale back operations, but my health and government subcontractors kept me busier than ever (as you might imagine).

As for the commercial office space — that’s a great example of what happens when things don’t go according to plan.

In 2019, I purchased a small office space in downtown Miami because I felt like I was wasting money renting office space at the local co-lab. My original plan was to work in part of the office and rent out the other portion to other small business professionals and freelancers.

And for some time, the plan worked. I was able to generate a small revenue stream and mostly cover the mortgage.

However, when 2020 rolled around, I was forced to shut it all down.

Luckily, the mortgage was small (this goes back to not biting off more than you can chew) and the rest of the business was able to absorb the cost. I also replaced some of that lost income by launching my blogs in 2020.

Having multiple and diverse income streams are absolutely crucial to not only scale, but also the overall longevity of a small business.

In the future, I plan on diversifying even more by continuing to grow the blogs and I am in the process of reopening my office space as we speak.

As you add additional revenue streams, be sure to look back at the big picture and ensure that one revenue stream won’t drown another if something doesn’t go according to plan.

What are some of the biggest lessons you’ve learned when scaling your small business? Let us know by tagging @collectivefin on social media.

Originally published at on July 1, 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.