Working independently isn’t for everyone, and I think it’s important to do some reflection before you make the decision to freelance. I’m going to walk through some questions I asked myself before I started freelancing, and some I wish I had asked.

Are you confident in your skillset?

This was a big one that was actually a motivation for me to freelance - I had been working in studio for three years, and knew how to run a project, all the steps involved, and what success looked like. While I think it is possible to freelance without prior experience, I think that it’s much easier and more fulfilling to have your base skillset be at a solid level before you make the jump.

If you ask yourself this question, and the answer is yes, you’re probably all set to move to the next question. Maybe you’ve worked in an agency or in house as a designer, and you generally know what your core skillset is, how to do it, who it’s for, and what success looks like.

If your answer is ‘I’m not sure’, I would encourage you to take a step back and look at your work from an outside perspective. Collect projects you’ve worked on, and pretend that you’re looking at the portfolio of a friend or peer. Does this person know what they’re doing? I’d bet the answer is ‘yes’ and you were being hard on yourself. I think it’s common to feel like your work isn’t ‘good enough’ yet, but often that comes from a gap between your taste and what you know is ‘great work’ and where you are now. The gap may be there, but that doesn’t mean you can’t work for yourself and close it. If after reflection, you’re “im not sure” turns into a no, then what?

If you ask yourself this question, “are you confident in your skillset” and the answer is no, it doesn’t necessarily mean that freelancing isn’t right for you, but it may be more difficult, and I want to be transparent about that. Learning how to freelance and run a business is a big task. If you are also learning your skill, at the same time you’re learning to freelance, you’re asking a lot of yourself. My biggest recommendation if you aren’t yet confident in your skillset, whether that be graphic design, web design, development, or copywriting, is that you learn from someone else, before you go out on your own. This was advice that was given to me when I was still in school, and I’m so glad I listened. Someone I knew in the design industry told me something to the effect of “make mistakes on other peoples dime and time, and when you know what you’re doing, go out on your own”

This isn’t to say that you should go work for someone else and be careless, or messy. But working for someone else is the absolutely best way to become confident in your skills, be exposed to business operations, and get a sense of what you like to do and are good at.

If your long-term goal is to work for yourself, or run your own studio, I would highly recommend pursuing a job at a small studio or company. If you can find a position within a small team, you are going to have a higher chance of seeing into the daily business operations, and having opportunities to touch different projects that may be outside your skillset, or involve collaboration. In house roles, or jobs at larger companies can offer a different type of learning and skill development, but particularly if your goal is to work for yourself, within a larger organization you run the risk of working on small tasks, and not having insight into the overall business. Being a part of a small team is an amazing way to build skills that are directly applicable to freelancing.

My only piece of advice if you are going to pursue a job at a studio before you jump into freelancing, is to think of it as more than just a stepping stone, and I would definitely avoid any kind of communication to the tune of “I want to work for you so I can learn how to run a business, and then I’m going to leave as soon as I know enough”. Someone hiring you wants to know that they are making a worthwhile investment in you as an employee. Go into any opportunity with the intention do your best work, with the best attitude possible. Giving your all at work might benefit your employer, but it’s also going to benefit you in your skills, experience, and result. An employer gets to benefit from your excellence for a short period, but you get to benefit from your excellence for your whole career. Keep track of your wins, make sure you are maintaining an active portfolio, and when the timing is right and you feel confident in your skills, you can jump independent.

Are you obsessed with your work?

Obsessed is a strong word. Maybe we can substitute it with ‘care deeply’, but at the end of the day the message is the same. Working for yourself requires you to be driven by a desire within to do good work, not because someone else said you should, but simply because you really really want to. Every single freelancer and entrepreneur I know is constantly thinking about work. You think about where your next project is going to come from, how to make the design a little bit better, how to solve that development problem you’ve been struggling with, if you were weird on that client call. It’s relentless and all consuming.

I also sometimes hear people talk about freelancing like it’s a break, or with optimism that they will have more free time. Working for yourself will very likely not give you more free time, but it will give you more choice in how you spend your time. I think about work pretty much every waking moment of my life, and I work more than most people, but I also go to the mountains to ride bikes, run errands mid-day, see my family regularly, and spend a lot of time at home with my husband. I have flexibility in how I spend my time, but work is always in the background.

It’s important for me to be upfront about this, because I think a big reason why some people struggle with freelancing is that they feel like they need to have balance right away. If you want to freelance long term, there will likely be a period where you do not have balance to start. It’s difficult to do good work. It’s difficult to build your client list. It’s difficult to build your reputation. These things take time and a lot of effort. Balance will come back eventually, but you should accept that it might not be balanced right away.

While this may be a reason that will cause you to pause on whether freelancing is right for you, it may also be the reason that you’ll be successful. I thought about work all the time before I started freelancing. I was always thinking about possible solutions to problems I was facing. But when I worked at a job, that relentless desire to do good work wasn’t rewarded. I made the same whether I stayed up worrying about a project, or whether I just went with the first draft. Freelancing is different. Every bit of effort that you put into work rewards you, either with more work, a boost in your reputation, or money. When you think about this question, if your answer is yes, you’re likely going to have a great time freelancing.

Do you enjoy responsibility?

One common theme that I hear from friends who quit freelancing, is that the responsibility of working for themselves was too stressful, too overwhelming, and generally not worth it.

This is going to be a very personal question, and require reflection on your part. Working for yourself means being responsible for every aspect of your job. Talking to clients, organizing timelines, saving for taxes, dealing with conflict, actually doing the work, talking about the work, finishing the work, invoicing, follow ups, long term relationships and more. It’s a lot.

I am someone who loves control and thrives in a self directed environment. If I’m in a group project, I want to lead it. If I set a task for myself, I’m going to finish it. I’m very self-motivated and don’t need someone to tell me what to do in order to make progress.

If that sounds like you, you’re probably going to have a great time freelancing. If that doesn’t sound like you, that’s okay. You may still enjoy freelancing, and grow to enjoy the responsibility, but there is nothing wrong with trying it and deciding that you prefer to work in another way. I would much rather be the person that tried something and have it not go as planned, then to have not tried at all.

Do you assume the best in others?

This is a mindset piece that I think makes a world of difference as a freelancer. Building and maintaining great relationships with clients is a foundational part of the work of freelancing. Yes, you have to do the creative work, but the rest is relationships. Talking to clients, communicating deliverables, managing the project, courting and closing new business. It’s all relationships. Humans are emotional and messy, and if you’re able to go into an interaction that has all the ingredients for conflict with a mindset of empathy and understanding, everything gets easier.

I try to assume that every client I work with is smart, capable, and a good human being. I treat every interaction and request with the kind of understanding and compassion I would want to receive. When there is potential for conflict, I try to take a step back and understand where the client is coming from. “Why are they asking me this?”, or “Is there something I missed that’s caused this?”

For example, let’s say a client responds to your message with a request you don’t understand. You send a final page design to a client and they ask for different photos, or flag a detail that seems insignificant. I think a lot of our gut is to be defensive and think “They don’t understand what I am doing, they are so annoying”. But what if instead you asked “Why are they making that request?” They may have asked for something that seems small to you, but makes a big difference in their business.

Approaching freelance work with this mindset helps to avoid a lot of conflict, and makes you someone that is easy to work with. It doesn’t mean you need to be agreeable to every ask from a client, but it does mean that you treat a client as an equal expert in the project.

Will you be able to support yourself and those who depend on you?

I have seen countless solutions and courses and templates advertised that promise to help you build a freelance business with steady income and massive growth, but none of them are perfect, and very few of them actually work. The nature of freelance work and project work in general is that of feast and famine. There’s no way to fully avoid it, but you can protect yourself from it somewhat. We’ll talk about specifics more in the ‘money’ chapter, but it’s important to ask yourself if freelancing fits with your real-world responsibilities.

If you work for yourself, are you going to be able to support yourself and those who depend on you? There are a few factors here including, do you have an emergency fund? Do you have a plan for health insurance? What if you don’t get work for a few months? What is your bare-bones income you need to support your life? Again, we’ll get into specifics in the money section, but I want to encourage you to be practical here. I live in Canada and don’t have to worry about a medical emergency bankrupting me. If you live in the US, it’s a different story, and I’m not going to pretend I know all of the intricacies of insurance coverage in a country I don’t live in, but please consider it before you make the jump full time.

On a more positive note, this question could actually be the reason that you want to freelance in the first place. I decided to freelance specifically because I wanted to make more money, to support my family in the future. I asked myself this question, and the answer was actually “I can’t afford not to try freelancing”. I knew that there wasn’t going to be a way to make the income I was after working in a local studio or agency, and that for my circumstances, the best chance of supporting my family was actually going to come from working for myself. That might not be the case for you, but asking this question will reveal some very important factors to consider.

Nothing has to be forever

If you’ve asked yourself these questions and your answer to each one is ‘yes’, you’re probably ready to freelance. If you had some ‘no’s or ‘im not sure’s in there, I would encourage you to think about this - no choice has to be permanent, but you’ll never know what kind of success you could find unless you give yourself a chance to try. Set out a specific time period where you are going to pursue freelancing with your full effort, and don’t make any decision about whether or not you want to continue until that point. Realistically, I think you should give yourself at least 8 months, but preferably a year. The first 3-5 months can be really rocky, and if I had to make a decision in those early days on whether I wanted to continue, I don’t know if I would have. But I had set out to freelance telling myself that I had to stick it out for a full year. Because I had given myself that time constraint in my mind, I knew that I had to give it my all for a full 12 months. By the time that mark rolled around, things had picked up, I was fully booked, and I had doubled my studio income. There was no going back. If you’re able to give yourself the grace of time, it can be transformative. And if you get to that expiry date and you don’t want to keep going, there are dozens of other ways to work. It’s okay to decide that it’s not for you, nothing has to be forever.