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The Freelance Roller-Coaster Is Real

One of the talks that I went to at Midwest PHP was Yitzchok Willroth's Getting off the Freelance Roller-Coaster. I talked about it in my Midwest PHP 2015 Recap and discussed it on That Podcast Episode 17: The one where The Force Awakens. It has become all that much more important to me over the last month.

This year alone, I've found myself without clients in the queue twice. In both cases it was unexpected and in both cases it was long before I thought the project would be over.

Two times.

I can make excuses that it wasn't my fault and that it was just bad luck that I found myself suddenly without work. It was my fault. I've made, and continued to make, a few bad decisions. Here are the things that Yitz talked about that I need to do better on.

All My Eggs in One Basket

It is oh so tempting to land a 40 hour/week gig from a great client that is rock solid.

"Just for a few months," I tell myself.

Must. Not. Give In.

No matter how solid the contract appears, I cannot ever assume that a contract won't just up and disappear on me unexpectedly. If it does, it is quite likely that I won't have something else running along at the same time meaning I'll be in a position where I'll have zero income until I can scramble to line up new work.

I don't think I should never put all of my time and energy into one client's project. I just need to remind myself what has happened two times in the span of just three months and ask myself if it is worth it to have no safety net.

@coderabbi talked about this at great length and I could feel my skin itching as I realized the position that I was in. I knew I needed to change but had not moved quickly enough to avoid getting caught in my own trap.

Always Be Lining up New Work

I've had it in my mind that as this last project was coming to an end that I would start looking for new work early enough to have something lined up in time.

Clearly I didn't start soon enough.

This is made all that much harder if I'm working with larger contracts taking up the majority (or all) of my time. It can be daunting to try and line up new work three months out, especially if I don't know that the current large contract will be done by then.

Some might be asking, "why wouldn't I know when a contract was going to be done?" Well, that is a great question and maybe another lesson for me to learn. Suffice it to say, this contract was hourly and there was no end in sight to the amount of work left to do. It seemed like a good deal at the time. Sadly the situation changed quite literally overnight.

In any event, what is clear to me now is that even with my best intentions, I probably wouldn't have started lining up new work soon enough. Even if I had been lining things up for a month or two out I could have taken this opportunity to say, "Good news, everybody! That project we were going to start in a month and a half? I can start right now!"

Plan Projects To Start at Different times

This was an interesting idea that I was sort of doing anyway. Scheduling everything to stop at the same time can be problematic. If all of the new projects fail to start up for some reason (as happened to me in January of this year!) then you find yourself in a pickle.

In my defense, I had planned one project to stop and an existing project to ramp up (it had been in a maintenance mode of sorts through November/December) in addition to firing up a brand new project. As luck would have it, the new project never actually got kicked off and the project that was ramping up was shut down just two weeks in.

What did I learn? That even if you do try to do the smart thing and offset projects you might still end up with no work. Still, it does make sense to not schedule all of your projects to end at the same time. It makes it less stressful to transition to new work instead of having to transition everything at the same time.

Hire a Marketing Company (Better Yet, Hire Two)

I liked Yitz's take on this. I'm a fan of hiring people to do what they are good at rather than you doing it yourself anyway, so even if he wasn't talking about hiring agencies to market you. I think he included talent marketplaces like oDesk in this.

This is one area that I've struggled with in the past. I haven't made connections with many staffing companies that are looking to help place people for part-time work. I'll admit I haven't looked too hard for this but almost all of the work I've had sent my way from agency recruiters has been for contract-to-hire work where the expectation is full-time and onsite.

As for the talent marketplaces, it seems like it has been hard to find quality leads from there. Mostly with oDesk.

In most cases it feels like oDesk is a race to the bottom. That isn't a game I can afford to play. The promising leads always seemed to pull a bait-and-switch and offer 1/4 what I had listed as my minimum and require the contract to be handled via W-2. In almost all cases, these annoying leads appeared to transition the relationship outside of oDesk.

Tim Lytle has had some success on oDesk so I think that I must have just been "doing it wrong" in the past. I'm going to have to give it another go.

I signed up for awhile back and have not had a ton of luck with it until just recently. I'm going to start actively pursuing these posts in the future to see if I can make this become a better source for marketing my skills.

My friend Hari K T suggested I give Toptal a try. I hadn't heard about Toptal before but it looks like it could be pretty interesting. I'm currently in the process of going through their acceptance cycle. They claim to only accept the top 3% of applicants so we'll see how it goes!

One place I have had decent luck is with some of the micro-consulting services like AirPair and Codementor.

I had a great first experience with AirPair several months ago but since then they have updated their site and I'm not sure I'm even connected anymore. There have been a few hits from there that were either well outside of my expertise or far below my posted hourly rate but the one solid lead I got out of it was pretty nice.

I also had a great first experience with Codementor. You can check out my public Codementor profle. It definitely helps to try and push people to these services if they provide a nice profile or landing page for you! I'd love to do more through Codementor in the future.


I've been learning a lot over the last year and a half about running my freelance consulting business. So far it has been rewarding but the first quarter of 2015 has been pretty stressful. Most of that is my own doing and I need to keep working on my process so that I can better avoid making these same mistakes in the future.