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6 Lessons I Learned from My First Year of Freelancing

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Celebrate! I just passed my first year freelancing full-time.

Freelancing has been a big change for me and I like to think that it was a positive one. Those around me know I seldom make ‘small’ changes.

However, despite my example, I see others around me considering whether they would be better off freelancing instead of maintaining a regular job, too. (Did I not complain enough?!).

I would love to share some of the lessons I’ve learned that might help you. And if not, perhaps you can lean back in your chair with added comfort, comparing your own experiences and see how much better your situation is.

Actually, when I got started freelancing I had a lot of support. I had a few great friends who were willing to bring me on for contracting roles and a fantastic mentor who guided me with plenty of practical direction. Sometimes that included ‘tough love.

Arguably it wasn’t tough enough, though.

Together with direct advice from seasoned experts, I read articles like these. I ‘heard’ what they were saying but didn’t fully appreciate the lessons until I experienced them myself.

While this might suggest that people considering going out freelance are unlikely to fully take on board what I share here, I hope everyone else is a whole lot less stubborn than I was.

One caveat. Originally, I was hesitant to write this as often topics like these can come along as a little pretentious. So I will say, just because I’ve learned some things doesn’t mean I have mastered everything here. In fact, I hope that my ideas will be even more informed in the coming years with experience.

With that said, here are the lessons learned from my first year of freelancing.

6 Lessons I Learned from My First Year of Freelancing

What services should I offer?

It’s a cliche to say that in freelancing but it’s all on you. Don’t forget that extends to more than just organizing your taxes and paperwork. Freelancing required me to think through all the potential services I could offer, and the people I could help.

This is strategic work that the company you work for has already worked out, proven, and refined.

What should have I done? Pick just a handful. Maybe 2 or 3 things.

What did I do? Offer everything.

But why is doing more not better?

Because more isn’t better. More is shorthand for ‘more complicated’.

Looking back, the times that were most difficult to manage were when multiple types of services were being delivered. Client expectations will be different, work requirements were different too.

Simpler, for me, is generally better. That means sitting down at a desk and running through the same kind of task all day, tastefully broken up with prospect and client contact.

One of my mentors once shared a great analogy on this. Your services are like products on the shelf. Some people can get away with having just 1 product if they have enough volume and it pays well. Being Amazon won’t make you more profitable by itself.

Admittedly, it is tempting to offer more and more. This is something I’m still working on, narrowing down to the most effective offerings and procedures.

Another consideration is that some tasks are inherently easier to offer freelance than others. Tasks that can be isolated to just yourself, such as copywriting, SEO or data analysis are easier than tasks that have a lot of collaboration with others.

How to do the work?

For every service, there should be a corresponding onboarding and execution process (another reason to focus).

This is part of being professional. Clients expect you to tell them what they need to give you (in one email, if possible) provide a plan, and do the work while checking in at the appropriate times.

Times this by 10 offerings and it can be chaos if you are building the ship while sailing it.

Follow-up reports, such as a list of work completed or stat improvements, I find are a nice touch as clients can see you are being transparent on delivering all that you said you would.

Yeah, it is extra work and it isn’t paid for. But when I haven’t done this, I’ve regretted it.

How to find clients?

Looking back, I’ve been very lucky to have received so much work by word-of-mouth and repeat business. But talk to any freelancer or agency and you’ll probably find out that this is pretty normal.

So to find clients, the answer for me was: quality work, relationships, and connections.

I did also meet some new clients using freelancing platforms and cold prospecting (via email and phone), though they were few.

Many people sneezed on freelance platforms but I feel they are worth the time and money if you’re starting out and building up a book of business. Some of the best clients (and now friends)

I’ve met have been through freelancing platforms.

Overall, it hasn’t been too much of a burden as it is often made out to be. After I was able to deliver work and gain the trust of a decent handful of clients the month-to-month work took care of itself from this book of business.

And that was the key lesson. To survive, build up a book of business as soon as possible. Sometimes this meant taking on cheaper clients/tasks in the beginning, but with quality relationships, the amount of work I had each month flowed in by itself.

How important are portfolios?

A portfolio is a way of proving that you can do for others what you are suggesting they hire you to do.

Having worked in the field where I currently freelance, my ‘portfolio’ was naturally built through work examples where I had the majority contribution and responsibility.

Looking back, I would have worked more around the edges to try to build up a stronger portfolio with more direct examples of what I wanted to offer. Work examples are the best evidence that you can get people results and know what you are doing.


How is the work-life balance?

As a freelancer, can you sleep in any day you want? Yes.

You can pop out to the bank for a few hours (slow service) or take an afternoon off if you want to. Also yes.

But with this comes two corresponding responsibilities.

Having to deliver what you promised by a certain time, no exceptions.

This isn’t a problem when things are organized. Though sometimes life happens. And sometimes you take on more than you can chew, or you just can’t maintain the motivation to work productively for a few days.

Thankfully, many clients are understanding and flexible with due dates but it isn’t a good look and certainly, the business relationship will be lost if delivery dates are missed.

Though if you are like me, sometimes this means taking on too much and being ‘on’ 24-7.

The other responsibility is needing to do enough work to pay yourself, even when you’re sick and tired. Often, taking breaks inadvertently eats into business development time, encouraging the ‘feast and famine’ cycle.

To date, the best way I’ve found to manage this is to actually keep regular office hours. It does tend to skew to longer hours than usual, but it does help telling yourself you can ‘turn off’ at the end of the day until tomorrow.

It was also interesting that working in an office-like environment actually boosted my productivity. Renting a dedicated workspace helped keep me in the zone and the days generally progress faster, letting the days fly by versus the crawl of working from home.

How do you get your finances in order?

A lot of the basic things here were as important as they were made out to be.

Register a proper business (even as a sole trader), get a business bank account, and separate personal from business expenses. Issue real invoices. Get help with your bookkeeping and tax filings.

The more I mixed personal with business, financially, the more work it was to untangle these later at tax time.

Keeping a buffer, both business and personal, helped smooth the income rollercoaster over the months. Something I don’t see often talked about, but it would be definitely worth getting in place first before jumping out full-time.

What I wish I had known

For those without the benefit of time, here are my key learnings summarised:

1. Pick a few services to start with that I can comfortably deliver alone. Simpler is better.

2. Develop procedures for each as soon as possible.

3. Build a book of business (work relationships) as soon as possible, even if it is just enough to survive.

4. Prepare a solid portfolio with direct examples.

5. Keep a rigid work schedule and find a dedicated place to work. Take weekends off.

6. Get simple financial and legal aspects in place, particularly banking and bookkeeping earlier rather than later.


Freelancing can be a positive move, full of interesting work and great clients. But non-work aspects easily make up 30-40% of the actual work that goes into being a freelancer.

I hope these learnings might be useful food for thought points for you so that you can have a smooth first year. If you are interested in my key marketing lessons learned, you can check out my article here.

Want to learn more about freelancing? Take my free 7-lesson mini-course Get on the Right Path to Freelancing here.

Images by chenspec and Noupload 

Benjamin Boman

Benjamin Boman is a freelance marketer and host of The Marketing Automation Discussion, a podcast that discusses automation strategies and techniques for B2B marketers and agencies.







This Post Has 3 Comments

  1. Hi Benjamin, Congratulations on your first year! I’m going on 4 years in the biz for myself and I love your thought on not making it complicated with services. I’ve done the same as well and kept the best money-making services on and dropped the time-consuming ones off.
    You learn a lot that the first year in business yourself such as not working 24/7 and how to manage money better.
    The stress is less as you get on in years with it, you go with the ebbs and flows much easier 🙂

    1. Hi Lisa,

      I’m so sorry I just saw this reply!

      Hearing that it was your experience too has been a great reminder for keeping things practical. Like you suggest, drop off the less practical ones.

      Thank you for sharing.

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