Side Hustle Story From A First-Time Freelancer

Today I am participating in a blog swap on lessons learned from side hustles.  The post below was written by Pilgrim, who writes stories and gives perspective on the road to financial independence at FI Journey.  You can find my post on the same topic over on his blog.  Thanks for this wonderful post today, Pilgrim!


As an IT Manager by day and father of 2 young children by night, I usually have plenty to keep me busy without the need for side projects. However, with 15 years of IT experience I also have a wealth of knowledge that friends and family glean from and make use of on a regular basis, and I enjoy helping folks when I can.


One area that I have a good bit of experience in (and I enjoy) is building websites. I’ve built a few for the company I work for, and I’ve built several personal sites for myself using various tools, all the way from FrontPage (back in the ‘90s) to hand-coding them in Notepad, working with HTML and CSS and now WordPress as much as I can. The changing landscape of web technology is exciting to me, and it’s why I love working in the field of IT.


So when a lady from my church stopped me outside one day and asked “do you think you could help me build a small website?” I was more than happy to oblige. We talked through a few ideas and a few details and I told her I would get a quote over to her for a simple WordPress site for her small business. Little did I know what challenges awaited me…


Delusions of Grandeur


I went home pretty excited and started working on a quote. Once I finished listing out the scope of work we had discussed, I started thinking about what kind of hourly rate I should charge. Website work isn’t cheap, but since this was a friend and I was somewhat inexperienced I figured I’d give a lowball price on the entire project instead of charge hourly. The price I gave ended up being around $25/hour, which is fairly low, for those of you with no exposure to website developers.


As the day went on I began to dream about what might happen with this project, and what my little “side-hustle” might turn into. Could this be the perfect job for me? Flexible hours, a hobby I enjoy, and a good hourly rate? In my mind, I was sure I could begin charging $50-$70/hour pretty quickly after a few introductory jobs. So I sat down and started drawing up a company logo in Photoshop, just for fun. I also registered a domain name that I might want to use for my own business website. There were dollar signs dancing in my head.


A Mushrooming Project Scope


frustrated man at laptop

Then reality set in. I sent out the proposal and my friend relayed it to her boss, who came back with a LOT more work that he wanted done, because at that price, why not?! They also decided that they wanted an entire section of their site dedicated to video content, and they wanted it to look and feel like In addition, they wanted some DVDs turned into online videos, so there would be some video editing needed (which is way outside my area of expertise), and they wanted years of old site content cleaned up and moved over to the new website, which originally they didn’t want done.


As I looked down the list of additional requests my heart sank a little. With a full time job and a young daughter at home, these requests were going to turn a 2-month-long flexible side-project into a 6-month-long marathon project. And instead of being the hero of the day I was now looking at being the bearer of bad news and having to say “no” to a bunch of their requests. However, I realized that telling them this information up front would be the best policy, so I informed them that I would help them out with some of their additional requests, but not all of them. It was an uncomfortable conversation for me to have, but I thought it went OK, and I was still happy to be “on the job”.


The Human Dynamic

Then came an email that totally threw me for a loop. The website for this small business had been previously designed and maintained by a close friend of the business owner, and they said that they weren’t comfortable with turning control of the website over to me. My friend let me know that they didn’t want to hurt the previous web guy’s feelings, despite the fact that their website looked awful and they couldn’t ever get him to update anything. On top of that they had discussed the entire project with this guy to get his input!


In his opinion WordPress was “of the devil”, and he strongly advised them against building a website on WordPress. I, on the other hand, had already explained to them the many benefits of WordPress, and it was exactly what they wanted for their new site. I knew it and they knew it. So to get around all this, they asked me if I would build the website, then teach their old web guy how to maintain and administer WordPress, so that “maybe he’d come around and want to help”. So to summarize, they still wanted me to build them a website, but they wanted me to work with their anti-WordPress friend and hand him the reigns once it was complete.


At this point I felt like my mind had just been made up for me. I called my friend and said “No thanks, this project is not going to work out”. What started as a win/win was turning out to be lose/lose, and I wanted to nip it in the bud before we even started. She wasn’t happy about it, but I’m sure she understood how things had changed since our conversation in the parking lot.


Lessons Learned


As much of a disappointment as it was to me not to be able to put together a solid side-hustle like that, the experience taught me several valuable lessons that have served me well ever since.


  1. Set expectations on the front end – If I had known more about how to communicate my abilities and limitations on the front end a lot of the disappointments I had during this experience could have been avoided.
  2. Price my time appropriately – Since this incident I’ve helped several other folks with website or computer work, and every time I give them my hourly rate up front, and now it’s set at an appropriate level. I’m worth every penny of what I charge, but it’s still a good price for most people. If it’s out of their price range they don’t move forward, which is good for both of us. If the project scope mushrooms then it’s still worth my time to handle it. In both cases we each come away satisfied with the price tag of the project.
  3. Set clear boundaries for myself – If I’m only willing to venture into certain areas, or only willing to spend a certain amount of time each week working on side jobs, I need to know what my boundaries are. Side projects can become burdensome very quickly if I’m not careful about maintaining my own priorities.
  4. Get used to saying “no” – This is a lesson many business owners have had to learn, but it really is better to be honest and upfront with a customer instead of over-promising and under-delivering.
  5. Prepare for the worst and hope for the best – Things can go south with a side-hustle at any time, so be careful with your expectations. Don’t burn any bridges with your day job, and be ready to change direction entirely if things don’t work out.


What do you think of this story? Have you had an experience “helping a friend” as a side-hustle, and how did that go? Do you have another side-hustle that you can tell us about?


photo from Free Digital Photos


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15 Responses to "Side Hustle Story From A First-Time Freelancer"

  1. Matt Becker says:

    It didn’t work out, but I think you learned some great lessons here that would help if you really do want to try and offer these kinds of services. One of the problems of working with friends is that the lines between business and friendship can get very blurry and make what should be normal business conversations uncomfortable. It sounds like you were right to get out when you did, but that doesn’t mean your side hustle idea can’t work. If anything, you’re much more prepared for it now than when you were dreaming big before.

    1. FI Pilgrim says:

      That’s true, thanks Matt. I would still love to move in this direction one day, but I’m a lot more realistic in my expectations now.
      FI Pilgrim recently posted..Smaller House, Larger Life!

  2. Wow. I’m so sad to know it didn’t work out. But yes there’s a lot of lessons to learn from that experience: before giving your hourly rate, you have to make sure you’ve talked to everyone involved first, you know all the things they want to be done.
    Marissa @ Thirty Six Months recently posted..Why I paid $4500/year for Car Insurance and How You Can Avoid That

    1. FI Pilgrim says:

      Thanks Marissa. Sounds like I need to think through my initial proposal process some more, that’s an interesting point. Do you mean you wouldn’t (or don’t) talk financials at all before meeting about the full scope of work? In a formal setting I can definitely see that, but how about when a friend asks you for some help? Would you go through the same process there?
      FI Pilgrim recently posted..Smaller House, Larger Life!

  3. I’m so sorry to hear it didn’t work out, and hope your relationship with your friend didn’t change because of what happened.
    Marissa @ Finance Triggers recently posted..Tools that make Personal Finance easy

  4. A couple years ago, my brother tried the same side hustle. My roommate was in the market for a site for his girlfriend’s athletics (she went on to win the Bronze for women’s long jump at the London Olympics).
    I worked out a deal where he did it as a portfolio builder. But my roommate didn’t have a clue what he wanted, took 6 weeks to answer my brother’s questions about the site design, never answered them fully, and didn’t even have any content ready aside from 5 photos and a bio.
    My brother did the best he could, but it understandably looked pretty amatuerish. Then the roommate got upset about the site and started dissing him, right in front of me! Needless to say, that roommate didn’t really work out.
    Edward Antrobus recently posted..Lessons Learned From Making Money On The Side

    1. FI Pilgrim says:

      Yikes, that doesn’t sound like fun. And it could have been such an impressive site to show off in his portfolio, too!

      There are a lot of prominent website developers out there that build a site around the content instead of the other way around, which sounds attractive to me. I doubt that works with your typical small business person, though.
      FI Pilgrim recently posted..How To Find A Great Deal On A New Laptop

  5. […] Evolving PF: There are some important lessons learned here from a failed attempt at earning money on the side. […]

  6. That sounds like a horrid experience! I’m sorry it didn’t work out for you. That’s too bad.
    SuburbanFInance recently posted..A Closer Look at The Shopping Environment

    1. FI Pilgrim says:

      Yes, it was frustrating at the time, but there were plenty of lessons I needed to learn and at this point I’m grateful for that experience!
      FI Pilgrim recently posted..Considerations When Waging A War On STUFF

  7. […] extra money on the side and the lessons learned.”  You can find my post on FI Journey and FI Pilgrim’s post on this blog.  Please check out the other participating blog […]

  8. moneystepper says:

    Its a shame that it didn’t work out, but I am personally pleased that I can learn from your mistakes. Thanks for sharing! 🙂
    moneystepper recently posted..Personal Finance Podcasts – A review of business, finance & investing podcasts

    1. FI Pilgrim says:

      Ha, thanks for reading and I’m glad to hear that it’s beneficial!
      FI Pilgrim recently posted..August In Review – Income/Expense and Net Worth

  9. […] This month I participated in a blog swap on the topic of lessons learned from my first side hustle.  My post at FI Journey was about my short career as a medical guinea pig and FI Pilgrim’s post on EPF was on building a website for his first client. […]

  10. airtonix says:

    To be honest, you did the right thing.

    But I agree that wordpress is utter crap (and so is anything php)

    If you want to be doing this job right, you need to know (at minimum):

    – git and how to feature branch, always deploy from master
    – compass and sass with zurb foundation
    – bower, grunt and npm
    – python, django and virtualenv
    – linux on the server and desktop (seriously it’s hilarious that people use windows for development)
    – stop using photoshop for anything unrelated to print

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