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cappuccino, headphones, hard drive and laptop

How to Work with Freelancers

I used freelance work to kick start my business. It’s perfect for that. You make new contacts, reacquaint yourself with old contacts, and if you’re lucky get a few referrals. As a bonus, you build your portfolio to showcase on your personal website. Freelance work is satisfying since you can build your own schedule, however you have to work much harder alone versus relying on a paycheck that comes reliably a few times a month. So, it builds work ethic and character to put it mildly.

What Are the Pain Points of Freelance Work?

Obtaining clients is the first hurdle, of course. For me, my first freelance client was a former boss. He has hobbies outside of his full-time business, and decided that he’d like to try to make some extra money from that hobby, so he hired me for regular video editing and market those videos. It’s a regular gig, so it’s great for me! It gives me something to work on monthly, and adds entries to my portfolio.

My second client was a former colleague. We both previously worked for the boss I mentioned above. She needed a website with very specific requirements. This was fantastic news, since I’ve been chomping at the bit to get a website build outside of my own.

Jhebert Roofing website screenshot

My third client was an acquaintance that I met as a result of a mutual contact. He helped found a local service company. They tried me out for a few months with odd and end things such as screen printed shirts, brochures, door hangers, etc. They were very happy with my work, and let me know that they were shopping around for someone to regularly handle their social media accounts, and their website. I put a proposal together and emailed it them. I made sure that I was fair to myself while still undercutting the agencies they were looking at. After all, what agency can compete with the pricing from a sole operator? Yeah, not going to happen. So, they decided to stick with me.

I migrated their website, revamped it (the design the prior agency used was very outdated)…set up the initial SEO properly for the website, and went to work on their social media accounts. They’ve been very happy with my services. We are currently discussing the possibility of me taking over their marketing for a sister company. 

I have also set up an Upwork account in order to fill in the gaps, and reach a larger (global) audience.

Getting paid in a timely manner is a pain-point worth discussing.

Overall, it hasn’t been much of an issue. I’ve been dealing with honest business owners so far. However, there are issues here and there that have zero to do with anyone trying to be shady, but rather logistics. First, you have to decide which payment methods you are willing to accept. Having several options is best so that your client has the least obstacles paying their bill. After all, you are a freelancer so if your client doesn’t pay you don’t get a paycheck, and that’s a huge downside to working for yourself. That’s when credit cards start getting maxed out, and stress levels rise. No one wants that.

Stressed woman with head in hands

Everyone is Busy

I’ve had clients who honestly forget, because they are busy running their own business and your freelance services invoice got lost in their overflowing inbox. I’ve also had clients who bit off more than they could chew in hiring me in the first place. They have a new struggling business, and didn’t realize that it takes a good amount of time before funds are regularly flowing in. While I understand their plight, I can only extend the billing deadline so far until it’s affecting my business. At some point, if they don’t pay their invoice I’ll be forced to take down their website, lock up their social media accounts, etc. I honestly do not want to do that. I always hope that it doesn’t come to that, and I will negotiate payment terms a few times before I have to take that final step. However, I don’t want my business to suffer due to my client’s over-estimation of their budget. These days, I’ve wised up and I’m setting up new clients with Square. The best way to avoid these problems is to avoid them, obviously.


The last billing issue that I’ve encountered is when you agree to take on a project for another agency (contract terms), and they’re depending on their client to pay their invoice before they can pay your invoice. I’m sure it usually isn’t a problem, but unfortunately my first job like this encountered this very issue. They’re chasing money and my hands are tied. It’s frustrating when you’ve been working on something for months and it’s finally time to reap the rewards and…nothing. You find yourself waiting and waiting. As a freelancer, I try so hard not to depend too much on incoming checks, because of situations like this, but sometimes you can’t help to. I run social media ads, Google Ads, print promotional items, mail postcards and all of this creates quite the bill. As you know, it takes money to make money, and I am my only investor. 

Who is Responsible?

At some point, I’ll need to hire my own freelancers to assist me as my client list grows. My responsibility to those freelancers will not change whether I’m paid on my end or not. I will pay those freelancers promptly and then hope I get paid from my client soon. The last thing I want is to burn a bridge with a reliable freelancer, because they didn’t sign up to chase money.

So, if you are a marketing freelancer keep in touch with me please…we may work together in the near future.

Overall, working for myself has been wonderful. I do work great with teams, however I work best alone, in my own office that’s in my home (with my cat – pic below) where I get to set my own schedule. I have very specific needs in terms of my working environment (I have Aspergers), so this is optimal.


Prior to Covid, I did work in brick & mortar offices for nearly 20 years, and simply reached a point that I could not do it anymore due to the social demands, fluorescent lighting, constant interruptions, frequent in-person meetings (that honestly should’ve been emails), and rigid schedules. I grew weary of being absolutely mentally exhausted by mid-week (to the point it affected my relationship with my wife), and constantly trying to work out the riddles that were my social interactions with co-workers. I’d have to take pages and pages of notes in every meeting so that I could decipher their slang, and short-hand later. If you know anything about those of us on the autism spectrum you know that we are intelligent and abstract concepts don’t escape us, but it does take just a little longer to process them.


These days, I simply make my calls when I have extra time to give it my complete attention, take good notes, and follow up later to confirm that I did not miss anything important. Yes, I’m working out of my home, but that does not mean my clients are put on the backburner. No, matter of fact since I’m in my idea environment you get my best work!


My hyper-focus is one of my super powers, and I can knock out days worth of work in 4-6 hours. A few of my special interests have always been marketing, graphic design, and building websites. When I have down-time I read up on the latest marketing strategies, knock out the latest Google Certification, or even take a Coursera course to obtain some new advanced skills. At the time of this article, I have obtained 8 Google Workshop certifications, 1 Google professional certificate, Apples Search Ads and 20 years of on the job experience. My wife doesn’t call me her “encyclopedia” for no reason.

Tortie cat with fish toy


A picture of my cat, Blanche, as promised.