7 Lessons Learned from Two Years of Freelancing

At the end of 2023, after working at HubSpot partner agencies for many years, I took the leap to freelance full time. 

It's been an incredible journey so far, full of ups, downs, and tons of unexpected challenges.

All of the cliches are true: the flexibility is incredible, the revenue planning can be scary, and normal business hours don't apply.

I know it's not for everyone. There's a lot about choosing this path that they don't tell you. But overall, it's been the most fulfilling part of my career.

Here are some of the biggest lessons I've learned so far. If you're a freelancer or thinking about taking the leap yourself, I hope you find them helpful.

1. Time Management is Critical

Being a full-time freelancer, especially one just starting out, means that there are very few external forces adding structure to your day. So, you've got to do it yourself.

Ultimately, it comes down to discipline—but I found a few really helpful ways to hold myself accountable. The most impactful has been to have an organized project management system (I use Teamwork.com) that documents everything I need to do and when for both clients and my own business.

Building some recurring tasks that I get done every Monday and Friday helps me bookend my week and ensure that nothing slips through the cracks. Those tasks include:

• Networking and sales outreach

• Accounting and invoices

• Creating my own content

• Research and skill-building

Of course, this is different for those who have kids at home or other responsibilities. For those folks, I imagine it's more about balancing all of the demands of your time and prioritizing dedicated time to get your work done in between.

2. Not Everyone Has the Same Quality Standards as You

This, of course, is totally subjective. And I know that I risk sounding a bit pretentious here.

However, this is something I keep noticing—particularly when working with other freelancers. The quality of standards is a wide range and there isn't always a single "right" way to get a task done.

Am I always right? Of course not.

But, if you consider yourself someone who operates at relatively high standards in the work you do, be prepared for others to operate at a totally different level from you. It can be frustrating at times.

I've been fortunate to work at a few places that held us to high standards and helped us develop the skills and expectations to a certain level. I recognize that not everyone gets that opportunity, and one of the best parts of working with others is to share what you know and learn from them in return.

The good news is that there are plenty of opportunities to encourage your clients or other freelancers you work with to do the work a certain way. You can try to set the standard or be an example, but there's only so much you can do when you don't work for the same organization (though to be fair, this is difficult even when you ARE part of the same organization!)

The bottom line is that you can only control what you do. So, focus on that and don't let the little stuff turn into the big stuff.

3. You'll Spend More Time Than You Think Just Chasing Payments

Like, a surprising amount.

Most of the time, this is just due to operational processes (invoicing systems, accounts payable, etc.) rather than any actual reluctance to pay on time. In fact, I've been really fortunate to work with many amazing clients that prioritize consistently paying their vendors quickly.

However, any business owner knows that chasing down payments comes with the territory. It's part of the job.

Be gracious and assume good intention, but don't be afraid to be the annoying person that follows up until you get paid. Advocate for yourself and your business.

4. You're Something Different to Every Client

Anyone who's worked at an agency knows exactly what I'm talking about.

For some of my clients, I'm effectively playing the Marketing Director role and managing large-scale strategy for the whole business. They don't have any internal folks with the right skill and experience to do this, so I'm managing everything from content strategy to social media to digital ads.

For others, I'm just a small part of a larger marketing team with a specific responsibility.

One client I'm working with, for example, has a robust marketing team of 5-6 employees and a really talented Director. They don't need help with their go-to-market strategy or optimizing their website—but they could use someone with HubSpot expertise to help them clean up their portal, create more automation efficiencies, and take anything HubSpot-related off their plate.

That's just one example, but if you're a freelancer then you've got to be prepared to wear multiple hats at the same time.

5. Don't Take a Single Client for Granted

I can't tell you how many times I've been certain that a client was going to sign on the dotted line. They're excited about your proposal and they know you do great work, all that's left is making it official with the signed agreement which they promised by the end of the week.

And then...crickets.

Priorities change. Budgets shift. Turnovers happen. Decision-makers can be slippery.

Be prepared for this to happen, and know that we've all been there. Some of my most positive and exciting sales calls ended up going cold on me. It's frustrating, of course, but that's sales, baby.

The important thing here is not to take it for granted. Don't fall for the trap (as I have done) when you're doing your revenue planning and say to yourself something like, "Okay Client X is signed through the next 6 months, and Client Y is definitely going to sign next week which means I'll hit this number in recurring revenue..."

Sales forecasting is an important part of running a business. Just don't take anything for granted until you have a signed agreement in your hands.

6. Flexibility is Key, Especially with Software

No kidding, right now I am managing tasks in Trello for one client, Monday for another, and Asana for yet another.

Plus, I use TeamWork for my own tasks. It's my favorite project management system (and I've used them all!)

Obviously, managing your work across multiple different systems isn't ideal, but that's part of the freelance game.

Where else do you need to be flexible with your clients?

• Schedules and meetings

• Review and approval process

• Billing process

• Everything!

7. Teaching is Part of the Job

Teaching is actually one of my favorite parts of the job.

Most of the time, I'm working directly with a SMB owner or president who has every little expertise in marketing besides general knowledge. They know they should be writing blog posts, but they don't know anything about search intent, keywords, crawling vs. indexing, etc.

(Many times they THINK they know about this stuff, but they usually don't.)

So, you've gotta teach them the concepts, the "why" behind the strategy.

Before you can convince someone that Colgate is better than Crest, you first need to make sure they understand that it's important to brush their teeth.

And truly, it's so fun to watch the lightbulb moments when these concepts start to click. It also helps with getting buy-in once they understand why we're doing what we're doing every week and are more willing to get involved, share their time, and prioritize marketing.