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#DearID Episode 50: Feast and Famine and Freelancing

In: Dear ID Showelearning

In this episode, I try my hand at answering one of the toughest questions around becoming a freelancer: How does that whole feast and famine cycle work?

Be sure to check out a transcript of the episode below the player. And the shownotes are here:

Hey everybody and welcome back to Dear Instructional Designer, the show about the instructional design journey. I’m your host, Kristin Anthony.

We’re in Season 4 of Dear ID where we are concentrating on the journey into freelancing as an instructional designer. Last episode, I related the strange and wonderful adventures that led me to freelancing, so I recommend that you check that out if you haven’t heard it and this episode, I’m going to try my hand and answering one of the most common types of questions about freelancing, and that is: How does that whole feast and famine cycle work?

One of the main worries people have about going freelancing is that it’s no longer a steady, repeatable income. If you’ve done any amount of looking into it, you’ve probably found articles, as I did, about the feast and famine cycle of freelance work generally, you know the state of work where sometimes you have a ton of projects all going at the same time and sometimes you hardly have anything. And that’s really scary if you’re supporting yourself or your family depends on your income. So I wanna tackle this in a couple of stages, if you will. First, I want to talk about an approach to thinking about freelancing that may be a little different than is instinctive, then I want to talk about ways to approach your freelancing career, and last I want to talk about ways to try and help yourself smooth out those cyclical bumps.

So first, thinking about freelancing. Certainly one way of thinking about it is that, oh, I’m going from having steady employment where I know what my paycheck will be to having very unsteady employment, and that’s true. But I think another way to look at it, that struck me when I first read it, is that freelancing is also going from having just one income stream to having multiple income streams. For most people, if you were to lose your job, goodness forbid, then you’d be completely without income. You’ve got nothing else coming in. But when you freelance, if you have to let one client go, which I’ve had to do, you still have three or four other clients. So one income stream drying up isn’t so devastating. To give you a personal example, in one of my jobs they went through this huge hiring spree right before I came, then a bunch of people left, then they did this whole reorganization and people who had been with the org for years were laid off, one of whom actually ended up dying of cancer a bit afterwards. So full-time employment, as I’m sure you all know is not a real guarantee of security, even though it feels that way. Freelancing is also no guarantee of security, but at the very least, you have the opportunity and the understanding among your clients that you will have multiple balls in the air, multiple projects running. So you don’t have to rely on only one client. Of course, there are some other big differences between freelancing and full-time employment (for example, you may be going from having one “boss” to having multiple “bosses”- although some of you might actually be dealing with similar multiple stakeholder-type situations in your work, so that may not be such a stretch), but I don’t want to oversimplify. I just wanted to point out that, while the idea of freelancing seems scary and unpredictable, I don’t think it’s really any more unpredictable than most people’s full-time work when you really stop and think about it and with freelancing there’s the benefit of being open and honest about having these other projects and your clients not being able to require that you only work with them.

So, the first thing, is that while I don’t want to downplay the risks in freelancing, I think it’s helpful to understand that they should be weighed against the risks of full-time, at will employment in our world. Second, there are absolutely several ways to approach your freelancing career.

Many folks with full-time jobs may be able to start by freelancing a little on the side. That’s how I started. There are a couple of things to keep in mind with this approach. First, you may need to check, possibly stealthily, to see if there’s any kind of moonlighting clause in your contract that might prevent you from doing side gigs or from doing sidegigs of a particular type or with a particular type of client. So, for example, when I worked for the software company, one of their clauses was forbidding that you work for a competitor for a year after leaving their employment. So you’ll need to check into that. Second, you’ll need to purchase your own equipment and tools. Because of clauses about work for hire and the use of technology, if you have freelance clients while you work full time, you’ll need to basically make the same kinds of investments that a full time freelancer would in terms of making sure that you have a computer that can handle the kind of work you want to do, purchasing subscriptions to whatever software you want to use, possibly including accounting software to keep track of expenses and send invoices, etc. You’ll also still have to think about paying taxes on this separate income. Last, but not least, there’s an opportunity cost for freelancing when you are also full time. Like I mentioned from my own journey, you’ll be coming home from work and then you’ll start working again. This can lead to burnout really quickly if you aren’t careful. Do you already have the kind of job where you bring work home? Then you may find yourself feeling overwhelmed if you also have to finish things for outside clients. Do you have a lot of after-work activities that you like to or need to do? Cooking? Chauffeuring kids to different practices? Running or yoga or martial arts? Working on client work after you get home can really interrupt those schedules.

Yes, you can and should discuss the expectation around your weekly commitment and timelines with the client up front, but in general, clients, like your full-time job, want a fairly fast turn around and that can cut into the other things you value in your world. So yes, you can take on clients while you work full time, AND think very carefully about the load you commit to, the number of clients you take on, and the possible opportunity costs.

Another approach is going full freelance. My advice would be, of course, to do some legwork up front. Building your portfolio and showing your work is absolutely the best thing that you can do to advertise your services. Thus far, my network and my portfolio have been the two things that have brought me all of my business. And that’s not an exaggeration: All of my business. I’ve been lucky and I acknowledge that but I haven’t had to search for jobs on upwork or apply for contracts (though those are totally valid ways of finding work and I’m not trashing them) but the work that I do in my side projects and the consequences of that work has been the number one thing for me. I want to talk more about this in another episode, but I’m bringing it up here because I consider it a part of the pre-work I did before going freelance. Your portfolio is essential. Full stop. If you don’t have one, make one.

Now full freelance gives you the opportunity to pursue several clients, but again, there are some things to think about. Like I just discussed, you’ll need to purchase all of your own necessities, such as accounting software, computer, back up systems, development software and, most likely, asset subscriptions (places to get icons and characters and things like that). But you’ll also want to think about things such as purchasing your own health insurance, paying all of your own taxes. One of the resources that helped me since I left my job after the open enrollment period for healthcare was the Freelancer’s Union and I’ll put a link in the shownotes. It’s a website for freelancers that is full of a ton of helpful resources, including a marketplace to purchase insurance if you’ve had a change in life situation, like leaving your job to take on freelance work. So be sure to check them out.

Without the pressure of full-time work, you may also find that you need to implement work systems for yourself that you may not have needed before. I have a huge dry erase monthly calendar on my wall where I plan out important dates such as paying taxes and sending invoices, record all of my meetings for the month, schedule in time for side projects or give myself appointments for things like seeing my family members in a dance showcase. I also have a huge dry-erase yearly calendar where I track vacations, deadlines that are far off, and conferences. And I have a smaller dry erase magnetic board that I use as a daily task kanban board so that I can concentrate on the small chunk of work I want to get done for each client on a daily basis. As you can imagine, I didn’t need all of these systems when I worked full-time, but now I do. They help me focus and plan and stay on top of all of the various personal and professional work I need to do. And that’s along with using my google calendar, Trello, and an app called Station that I just started using to create a distinct work environment of apps in an attempt tame my Monkey mind and try and prevent distractions. You’ll need to figure out what works for you, but I’d be willing to bet money that you’ll have to do some things differently than you were doing at work to make sure that you don’t drop the ball and that you stay on task. Depending on your personality, full-time freelancing can have its own issues. For example if you find yourself getting lonely or feeling cut off, you may want to make time to join local meetups or professional organizations like ATD or to work in a coworking space, which can be an extra expense. If you find yourself getting distracted, you’ll need to find some ways to buckle down and concentrate (when I was completely burnt out but still needed to work, I found the pomodoro technique to be a lifesaver). And if you find yourself working too much, you may need to set some boundaries, some exercise or other mini habits, and maybe even raise your rates (I know, that’s super scary).

The last option here is to split the difference and work part time with an employer and freelance on the side. To be honest, especially as I was going through the roughest patch, this was my ideal. I thought, how great would it be to be able to be in a more technical or programming-focused position somewhere and be able to continue to do learning experience design-focused gigs as my other half. And I event pursued that a little last year. It hasn’t quite come to fruition yet, but I’m still very open to it. I like the idea of being able to have those two environments and that may resonate with you as well. However, this may be the most difficult balance to attain. You’d need to find part time work for some organization or possibly be able to talk with your current employer about going down to part time and then you can also concentrate on finding some clients. If you can manage it, I feel like it’s probably a best of both worlds situation. Now again, you’d need to still worry about all of the things we’ve been mentioning, getting the gear you need for freelancing, taxes, possibly healthcare, and keeping an eye on your responsibilities so you don’t feel overwhelmed or get burnt out.

Which of these is best is completely up to you. Freelancing on the side, full-time freelancing, and part time job and part time freelancing are all completely valid. People have been successful with each approach. What makes the difference is being able to make the sacrifices that each of them would require worth it to you. For example, if you dream is to go full time freelance but you want to start by dipping your toes in the water and building up your client list by taking on one or two clients while you work full time, that’s awesome. There’s nothing wrong with that; It works. Just take into account what you might have to sacrifice for a time as you work towards that goal. Or if you decide that you’re ready to move into full-time freelancing, that’s awesome too. Just take into account that, unless you already have a client base, you might need to tighten your belt a little at the beginning and you may need to concentrate on building your portfolio and showing your work, as you make sacrifices to get yourself up and running. So it all depends on you. All approaches are valid and doable.

To recap where we are so far, first as you delve into freelancing, it’s helpful to think about it from the point of view of diversifying your income streams; second, you’re free to approach freelancing either full-time, as a side gig to your full time job, or part-time with your part-time job. The approach you take depends on what you feel comfortable with and what you’re willing to work with. So the last thing that I want to talk about is feast vs famine. How do you deal with the lean times versus the go-go-go times? My answer so far has been, to steal from Glengarry Glen Ross, Always be Looking.

With each client, you’ll be under a contract with them, either for a particular project or a length of time. You need to always have an eye on this and be thinking about where your next client will come from. Now, the most ideal situation would be for your current client to ask you back to do more work. This is a very real possibility, so as your contract begins to wind down, you should be sure to schedule a meeting to talk about how they’re feeling about your work quality (are they happy with the results?) and ask about whether or not there is any future work you might help with (they might even approach you about renewing your contract!). But you should also be continuing to look for other clients. For example, when I was starting out and had one big client, I cold tweeted one of my current clients because I saw that they were doing cool game-building stuff and I asked if they needed someone with my skill set. I had a google hangout with the CEO which led to him trying me out for one project that has led to many others. I also took every email that came to me from potential clients seriously. You might not want to take on every job, and you would want to take a hard pass on anyone who looks like they might be asking you to work for free, but for serious sounding people, it almost never hurts to just schedule a phone call with them and see if they’re a right fit. If they are, you might be able to schedule your work with them in such a way that it starts ramping up as other clients wind down. If they aren’t a good fit now, they may come back to you later for a different project and that may be a good fit. I think that the feast and famine cycle really grips you if you aren’t keeping that eye out for your next client. I’ve had phone calls with several clients who haven’t quite worked out, but who I’d definitely reach out to again in the case of some other client work dwindling down because they seemed like they would be great to work with. That’s one of the ways you build your network. Even if you can’t say yes right now, and as I’ve been preaching this entire episode be careful about what you say yes to, taking the time to meet with a potential client begins a relationship that you may want to build on later.

Another parallel approach to consider here is to think about your pricing strategy. Many of us default to hourly pricing. And that’s fine and valid, but of course, under this model, if you aren’t working, you aren’t being paid. So as you negotiate with the client, you may want to talk with them about number of hours per week. Can you two agree on a min and a max number of hours per week? That way you can better calculate your expected income. And this is not some crazy, out of the box things. It’s perfectly valid, as you’re talking with a client about the project and the timeline to say something like, “I can commit 8 to 10 hours for this a week which would give you a turnaround time of X. Do you think we’d be able to organize the work in weekly chunks like that?” And get yourself a sense of how you can organize the work for an expected effort every week and an expected income.

You can also think about pricing yourself in terms of the project. Instead of hourly, you might try to calculate a project cost (I read about this described as value-based pricing) and work with your client to set out a payment schedule for the project. For example, an estimated 6 week project that will bring the client Y value. You calculate the project cost and the client will pay you a certain percentage up front, a certain percentage at an agreed upon milestone and a certain percentage at the end. The advantage here is that the amount you make isn’t dependent on the number of hours you work and so it’s easier to rely on it.

You can use these strategies (always be looking and thinking about pricing) together and you might find that different pricing strategies work better with different clients. But I think as you continue to seek relationships with possible new clients and look for ways to more reliably calculate your expected income, you can smooth out, though perhaps not completely eliminate, the feast and famine cycle so that you can eat all the time.

I really hope that was helpful. Be encouraged if you want to start along the road to freelancing. There are so many valid and workable ways to approach this. You don’t need to jump in head first, if you’re not comfortable with that, and in fact, in every situation, there’s some important legwork that you need to do first. This is a question I’ll be trying to get to with each of our guests this season so you can hear other perspectives. I’ll also put all the resources I mentioned and anything else I can find in the shownotes.

I would love to hear from you. If you’ve got any follow up questions about this episode or any new questions that popped into your head about the freelancing journey, feel free to reach out to me. I’m @anthkris on Twitter, or you can shoot me an email at kristin AT

And don’t forget to leave a review on iTunes! Your review helps other people find the show and lets me know how I’m doing. I would really, really appreciate it.

Thanks so much for listening and I will see you back here next time. Take care!