How to Avoid Freelancing Problems Before They Arrive

Four years ago, I had an idea that most freelancers get when they’re a few years into their career:

“Maybe I should have a team.”

It sounds great, di ba? My job will be finding and getting clients (which is one of my strengths), making sure that all the tasks are organized (which I do for my own work anyway), and hiring skilled workers (I’d love to give work to other Filipino freelancers). I’ll pay the skilled workers above average rates ($15 to $50 per article, depending on skill), while I’ll charge the client what I normally charge and call it “profit”. What a great idea, win-win, I thought.

It was a great idea – in theory. In just 3 months, I encountered a lot of problems I didn’t expect:

Problem #1 – It’s hard to find good workers who could fit me into their sked! Sa dinami-dami ng Filipino freelancers, I had to find people who were skilled, understood and agreed with my vision, self-directed, and reliable. But most of the people I wanted to hire were too busy already! In all my searching I found exactly 3 people to work with, and one of them had to return to a full-time job.

I wasn’t even looking for “rockstars”, yet I found it very difficult to look for skilled workers who were self-starters (meaning: they are competent and confident enough to decide things on their own and not ask me permission for everything). I even hired a couple of other people who didn’t exactly meet my criteria pero pwede na – but this became problematic later on.

Problem #2 – I ran into the “hamster wheel problem”, where I had to keep looking for clients to keep the business profitable, but adding new clients often meant hiring additional people (who would be more familiar with their topics/industry), and hiring additional people meant I had to look for more clients to keep the business even profitable and cover all the time and energy I spent looking for clients and managing people.

Problem #3 – It turns out I spent most of my time being a middle-manager – something I did NOT want. What I really wanted to do was create quality content, take care of clients or do marketing. I did not want to spend too much time holding the hands of professionals like me, or training them, or reading 11-paragraph explanations of why they couldn’t submit their work on time. While I did end up with 3 good colleagues I respected, I needed more than them to service all our clients and the hiring process became unbearable after a while.

So eventually, I shut that down and just worked with the clients privately on my own.

Pero ito yung masakit – I could have easily avoided those problems! A year after I shut it down, I talked to an entrepreneur who ran a similar business model, and he said something like:

“The agency model is tough. You have to look for new clients to make money, but when you get new clients, you have to pay for more workers to service them, then look for new clients to make even more money! It’s a vicious cycle. You’ll spend the entire time being a manager!”

If I just talked to people who had been there, I would have known early on that the agency model was not for me. I did not want to be a middle-manager. I wanted to create things. I wanted to collaborate with talented Filipino freelancers, not manage them. All I had to do to avoid that super stressful experience was to ask.

Imagine that, 3 minutes spent posting a question in a forum full of entrepreneurs could have saved me a year and a half of stress.

The Matrix. Dir. The Wachowski Brothers. Warner Bros. Pictures, 1999

The Matrix. Dir. The Wachowski Brothers. Warner Bros. Pictures, 1999

Look Into the Future, See Problems Before They Arrive

Are there any upcoming obstacles to your freelancing career? The best way to know for sure is to look up people who have already made the mistakes you’ll be making and successfully overcame the obstacles you’re about to face.

In other words, here’s what you can do today:

Step #1 – Look for 5 people online who have done the work you want to do. If you already have specific people in mind, that’s great. If not, you can look for online forums or FB groups where people like this hang out.

Step #2 – Ask them about their major challenges. If you’re new to freelancing, you can ask: “What challenges did you face in your first 2 years of freelancing that you didn’t expect? How did you overcome those challenges?”

Or if you’re looking to try a new field or new approach, you can tailor that question accordingly. For example:

  • “For those VAs here who now manage their own team, what unexpected major challenges have you faced so far? How did you overcome those challenges?”
  • “For those freelance writers here who have shifted from doing rewritten articles or SEO articles and are now doing higher value work (writing sales copy, writing blog posts, etc.), what difficulties did you experience with the transition? How did you face those difficulties?”
  • “For the freelancers here who have been working with clients outside job bidding sites, what unexpected problems did you encounter?”

Step #3 – Then, wait for the answers. Your internal response to these challenges will tell you kung gusto mo talaga yung path na ipu-pursue mo. Every choice we make has challenges or obstacles attached to them – that’s just the cost of pursuing anything in life. Are you ready and willing to face those costs? If the costs are more painful for you than the potential gains, then maybe it’s not the right path to take.

Step #4 – Don’t forget to thank the people who answer your question. It goes a long way, especially if you offer to help them or provide value in any way.

Help out other Filipino freelancers like you?

Now to the important part: let’s help each other out. Remember, this is a COMMUNITY. I’d appreciate it if you guys help each other out. So here’s what we’re going to do in the comments:

For Experienced Freelancers (freelancing for more than a year): Leave a comment about

  1. the type of work you do and
  2. Your answer to today’s general question: “What challenges did you face in your first 2 years of freelancing that you didn’t expect? How did you overcome those challenges?”

For New or Starting Freelancers: Leave a comment about

  1. What type of work you want to do
  2. Any questions you might have for those other Filipino freelancers who are more experienced
  3. Also, don’t forget to keep checking the comments within the next few days – someone might have already answered your question!

3 thoughts on “How to Avoid Freelancing Problems Before They Arrive

  1. Jovell Alingod

    I’ll just be an agitator here first. 😀

    “Maybe I should have a team.” – Ha! Had the same thought last year and the hubby still thinks it’s a good idea. But I soooo completely agree with you on all the headaches you’ll get and Problem #1 is the root cause of all other problems after that.

    “Your internal response to these challenges will tell you kung gusto mo talaga yung path na ipu-pursue mo.” – Our gut is often a good guide (especially for women, I think). If it fits with your personality, interests, passions, you’ll light up and feel excited. If not, even if it means more money, you’ll have that sense of dread even if you don’t understand why.

    And lastly, your call to action really compelled me to comment. Ikaw na!! 🙂

    Now onto the questions:

    1. I’m a freelance writer and my services are focused on web content.
    2. A. The main challenges I faced in my first 2 years of freelancing were the ff:
    – I needed to learn a lot of new things (tools, terms, etc.)
    – I didn’t know how to choose a niche and target market for my services
    B. For the 1st one, I had no other choice but to give time to learning new tools and understanding how businesses ran online. For the 2nd challenge, it was a matter of being mindful of what types of tasks I liked doing. Re writing – I reviewed what types of articles I enjoyed doing and chose to focus on those which felt like play when I’m working on them. The process was the same for choosing my target market. I reviewed my past experiences with clients and used that as the gauge for my preferred clients and projects now.

    Reply
    1. Celine (Pinoy500.com)

      Thanks for your input Jovell! You’re right – it’s very likely that Problem #1 was the root cause of everything. That’s the thing kung medyo mataas yung standards mo I guess, the people you want to work with can afford to do their own thing (not necessarily because of money, but bec of confidence, competence). I did have a workaround later on – get the client to directly hire specific individuals and parang editor lang ako.

      Plus my mentoring helps kasi mas marami akong nakakainteract na freelancers personally, so alam ko na agad from a direct perspective the kind of worker a person will be just based on the kind of “student” they are.

      “For the 2nd challenge, it was a matter of being mindful of what types of tasks I liked doing. Re writing – I reviewed what types of articles I enjoyed doing and chose to focus on those which felt like play when I’m working on them.” This is a pretty good system.

      Question, though: what tools did you have to learn in your line of work? Plus how did you try and understand how businesses ran online?

      Reply
      1. Jovell Alingod

        Hmmm…as for tools and other things I needed to learn, there’s wordpress, basic html, cloud storage drives, pati basic email management and online calendar usage…pero often learn as you go ang approach ko.

        As for learning how online businesses run, I read a lot of sites talking about this topic, I also asked my clients if I can’t understand something. My questions would be like – why is this task needed, why is this task important for his business, what impact will it have if we do this or not? And most of my first clients were patient enough in sharing what they know with me. 🙂

        Reply

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