Lessons Learned While Starting a Freelance Business

After nearly 20 years working in SEO within agencies, I decided it was time for a change last year. I wanted a new challenge and the chance to grow in ways that my agency roles hadn’t allowed. So, ten months ago, I took the leap and started my own freelance SEO consulting business. It’s been an exciting, sometimes difficult, but ultimately rewarding journey. Here are the key lessons I’ve learned along the way.

The Shift from Agency to Freelance

Transitioning from a long career in agencies to running my own business brought some predictable challenges and a few steep learning curves. As an agency employee, I had the safety net of a team—dedicated salespeople, legal experts to handle contracts, and a steady stream of clients provided by the company. Suddenly, as a freelancer, all of those responsibilities were mine alone.

I wasn’t entirely surprised by how much there was to manage — I knew freelancing wouldn’t be easy—but it was still a lot to take on. From finding clients to negotiating contracts and handling administrative work, I had to figure out how to wear every hat in the business.

Building a Foundation

One of the smartest things I did was leverage my existing network. Before leaving my agency job, I was already in talks with a friend about a potential contract. That connection turned into a major six-month project — managing a massive website migration involving more than a million pages. This gave me financial stability and confidence during the critical first months of freelancing.

I also leaned heavily on relationships I’d built over the years. Posting on LinkedIn about my new venture brought referrals from people I’d worked with in the past, and their trust helped open doors to new opportunities. Networking made all the difference, and I’d advise anyone considering freelancing to focus on cultivating those connections well before making the leap.

Adapting and Learning

Starting a business meant learning a lot on the fly. I spent countless hours researching templates for sales decks, contracts, and other tools I’d need to land and manage clients. Thankfully, my years of agency experience prepared me to handle sales calls and customize materials to fit my style and services, but the process was still slow and involved plenty of trial and error.

For anyone starting out, I recommend doing as much prep work as possible about running a business, like contracts, sales, taxes, and creating an LLC. Research, learn, and gather the resources you’ll need to hit the ground running. It won’t eliminate all the challenges, but it will make the transition smoother.

But you can’t prepare for things you don’t even know you need to prepare for. I’ve had to learn some hard lessons through experience. For example, one client of mine is a large organization who pay their vendors in multiple ways – direct deposit (ACH), mailed check, or Mastercard. Mastercard was the fastest way to get paid, so I went with that one.

Huge mistake.

You can’t just deposit a virtual credit card into your bank account. You need a payment processor. I ended up paying for Quickbooks (this was a good decision in the long run anyway, because it made invoicing other clients a lot easier), but there are bunch of hoops you need to jump through to pay yourself with a credit card in Quickbooks.

And after finally getting the payment to go through, I learned my hardest lesson – there’s a 3% credit card processing fee! There are no warnings about this when you submit the payment, so I found this after it was already too late. I lost $800 of my earnings. That was tough.

There are other hard lessons to learn too, like how organizations have different net 30/60/90 payment policies. It’s tough to work for a month and not get paid for it until two months later. Or having to remind a client to pay their invoice – that’s not fun and it’s even a little scary, wondering if they’ll pay it.

It Can Be Lonely

I’m fortunate enough that my wife also works from home, so I’m not alone all day. Otherwise, this transition might have been much harder. But my wife is working on her own thing and she works in a completely different field than I do, so I can’t talk industry with her. My previous agency was fully-remote, so I’m familiar with working from home, but we had daily morning meetings, team meetings throughout the week, and I was a manager, so I also had one-on-one check-ins with my team. I was in a lot of video calls nearly every day. That all went away when I went out on my own.

This is where online communities were a life-saver. I thought about this before leaving my agency job, so I signed up to two paid communities more than a year ago; the SPI community created by Pat Flynn and the HeyCreator community created by Darrell Vesterfelt and Matt Ragland. I’ve also recently joined Liz Wilcox’ Email Marketing Membership community a couple of months ago.

These communities serve multiple purposes for me. For one, they all have a main focus, which is education in specialized topics and areas where I want to grow my business. And they give me a place to talk to like-minded people. These communities aren’t free but I feel have been absolutely worth what I pay for them.

Pat Flynn’s SPI Community (affiliate link) focuses on entrepreneurship and teaches digital marketing of all kinds. He covers subjects like building a channel on YouTube, podcasting, email marketing, affiliate marketing, brand building, business taxes and everything else that a business owner should know. His team also does weekly live presentations and Pat does a weekly office hours where you can join live and ask any question you want. Pat serves on various boards and advises several large companies, so he knows a lot.

HeyCreator is similar to SPI, but they’re on a much smaller-scale (and much more affordable). They also focus entirely on creators – people creating content on YouTube, social media, and podcasts. Matt also covers topics around productivity and being a solopreneur. HeyCreator does weekly live presentations and office hours too, with audience involvement.

And Liz Wilcox’s Email Marketing Membership (affiliate link) focuses entirely on email marketing. She also does weekly live video calls with the audience and provides the community with access to previously created content and new email templates regularly.

All three of these communities make me feel like I’m still part of a team, I can talk to people live, and I can ask questions of the hosts and other members of the community.

Don’t Sell Yourself Short

When I announced I was going out on my own, a lot of people in my network reached out to me expecting to get extremely cheap services. Former colleagues, clients, and agencies I had worked with in the past thought I’d be working for a fraction of the cost of working with an agency. While I do consider my rates more affordable than a lot of agencies, I’m not cheap.

Maybe people don’t immediately see freelancers as business owners. But that’s what you are, even though the only employee is you. You have to pay high taxes on your revenue, buy software, contribute to your own 401k, buy your own computer, hire a bookkeeper, and pay for insurance (both business and health). That adds up. You can’t expect to stay in business long, at least not happily, if you’re charging normal employee hourly rates. Overhead is why agencies are so expensive. As a contractor, you have a lot of the same costs. You’re basically a one-person agency.

For additional context about rates, I have a good friend who is also a contractor in this industry, and he advised me to go no lower than $175 per hour, considering my level of experience (20 years). I didn’t go that high, but I certainly kept that number in mind while I was setting my rates. That’s something to strongly consider when you decide what you want to charge.

You Don’t Get Paid Time Off, But You Can Take Time Off Whenever You Want

One of the great advantages of freelancing is being able to take a day off whenever you want. While you still need to be available for critical client needs (if they arise), for the most part, you’re in charge of your schedule.

But here’s the catch: there’s no paid time off (PTO) in freelancing. Unlike a full-time employee, if you take a day off, you’re not earning anything for that day. This reality can make taking time off financially challenging, especially when those unpaid days start adding up.

For instance, last year I took a two-month trip to Germany. I decided to take the first week completely off to explore the country, and then worked remotely for the remainder of the trip. While it was absolutely worth it, that single week off significantly impacted my earnings for the month. It was a stark reminder that, as a freelancer, you have to weigh the cost of taking time off against your income.

Finding Balance and Control

The most rewarding part of freelancing so far has been realizing that I’m not only surviving — I’m thriving. After ten months, I’m earning as much as I did at my agency job, but with half the hours. The extra time has given me freedom and control over how I work and live. My goal is to have anywhere from three to five clients, which I think adds nice diversity to my client list (and is important because you will run into client churn and have slow earning periods), but I’m happy maintaining a balance that allows me to focus on quality over quantity.

Encouragement for Aspiring Freelancers

If you’re thinking about freelancing, my biggest piece of advice is to plan ahead. Build your network, and if possible, line up a client before you leave your job. Having that safety net made a huge difference for me.

And if freelancing is something you’ve been dreaming about, don’t let fear hold you back. You only get one life, and it’s worth taking risks to see what’s possible. If it doesn’t work out, you can always go back to a traditional job, but if it does work out, the rewards — both personal and professional — are more than worth it.

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