Hard Lessons I Have Learned in a Year of Freelancing

It was almost one year ago that I said "good-bye" to my bi-monthly paycheck and a 9-5 working for someone else life. I have never been happier with the choice I made to pursue my own business. It was a scary leap but one I am so grateful for every day. It has given me freedom, the ability to pursue a wider range of work, the chance to work with so many new people and finally, I can take advantage of my type-A personality and control my own working life.

It has also come with some pretty harsh lessons I guess you can never be quite prepared for. Some of them, people warned me about ahead of time, but until you go through it for yourself, it really does not make a dent in your choices. I was lucky enough to have someone there to back me up every step of the way, emotionally and financially. This has made such a huge difference, but so many of the lessons I was going to learn the hard way to make better decisions the next time. This are true for me, but are not necessarily true for all freelancers or people with their own businesses.

1. You cannot hang your hat on any work you have currently
In the beginning, I thought that when someone said they had a project coming in that they wanted me to work on, it was a guarantee. I also thought that work I had now was going to stay for a while. This has almost never turned out to be the case. I am hunting down new work all the time. I would say more than 50% of the time, potential projects never happen or they are on hold until a later time. If I waited for all of those, I would never be working. I have had to learn to be in contact with people all the time to keep stirring the pot of future work.

2. Take out 30% or more of every check you get and put it into an account you never touch to pay for taxes
It is tempting to think that the money you get you can spend right away. Come tax season, you could be in a for a huge shock when you suddenly owe and you have already spent that money. In a regular job, all that is taken out for you so you never notice it is gone. Like all of your accounting and paperwork, taxes are up to you as the freelancer.

3. Workflow has its extreme ups and downs
You have to be prepared to have time when you can barely keep up and you work early in the morning and late at night. This can last for weeks at a time. Being that busy is great sometimes because you are making more money and you are staying busy. There are also extreme times where you literally have no work coming in at all. This can be hard because you have no money coming in, it can be long and boring and also creatively and emotionally straining. This can also last a long time with no real knowledge of when it might end.

4. You might be doing more production than design work This has its ups and downs as well. It is expensive for company's to hire a freelancer and what they might need is someone to do the down and dirty work. It is up to you to decide if you want to do this or not. This also may mean doing your own creative work on the side to keep doing projects you enjoy.

5. You have to make money to freelance. This was also a very hard lesson for me. It comes with a lot of freedom but at the end of the day, you still need to make money. It is not all about doing what you want to do when you want to do it. Pick and choose but do not be too picky if you want to keep afloat.

6. Some clients are more trouble than they are worth. I don't know of another freelancer who would not agree with me on this. It may be that you have to hound them to get paid. It might be that the amount of work versus the compensation is unbalanced. It may be that their approach and personality is hard to deal with. Or it may be that the work is not satisfying. In each case, you have to decide where you are and what are your priorities. Each week, this changes for me based on workload, scope and style of the project, the client and money flow. You have to do work you like and keep incoming work as well.

7. You have to say "NO" to work sometimes.
This is very hard as a freelancer because you never know where the work is going to come from. This means it is very tempting to say "YES" to everything just in case you have a dry spell. This works sometimes, but it also can mean you have way more than you can handle and you will get burned out. Listen to your instincts. If it feels wrong, it might not be for you.

8. Take a break sometimes.When I started, I had the feeling that I really had to prove myself. I worked all the time and never took a break during the day. Then someone told me that if you worked a regular job, you would talk to co-workers and walk around once in a while. Now, I take advantage when I have some downtime to work out of the house, work a different schedule or go to the gym during lunch.

9. Find other occasions to socialize and network. This has been the hardest for me. I have a quiet personality and so do not notice much being alone during the day. Eventually though, it can get to you. Try and work outside of the house with other people, see friends on the weekends and network to make some new connections. Network as much as you want to to seek out that next piece of work, but also, just to talk to other people. I also like to work on-site sometimes just to have connections with people during the work day.

Overall, freelancing has been great to me so far. Harsh lessons sometimes, but never regrets.

What Have I Learned From Teaching?

When I originally decided to take on design teaching as part of my freelance life, there were two main reasons. One obvious one was to have some income during lean times in freelancing. The other was to try and impart some important things I hold near and dear that I learned when I attended art school and that I acquired in my professional life. How could I express to people and have them be as passionate as I am about good typography, the fundamentals of design and having a strong concepts behind every design?

I went into teaching with, I think, very uptight attitude about the whole thing. I went through hell in art school with the workload, tough critiques and other challenges. I think the whole experience made me a stronger designer, and so I wanted to teach the way I was taught. Tight structure, controlled syllabus and constructive critiques was the way I started. OK, sounds reasonable, right? Well, easier said than done. I quickly realized that teaching outside of my immediate experience was going to need constant tweaking and adjusting based on the students and their skills.

My fourth teaching experience was at MCAD with students in a partnership with a local high-school. This was the experience that immediately had me learning so much more than I think I have taught them.

1. Sometimes, approaching students gently rather than harshly yields better results.
As hard as this is for me to admit, because I am a total no-nonsense type of person, I cannot expect all students to be like me in their approach and focus.
2. Encourage as much as possible
Especially with my high school students, I want them to keep coming to class and finish school, so small victories may lead to something bigger.
3. Keep critiques as interactive as possible, but do not push it further than it can go.
Some people are not going to be good at this and I cannot only push the class so far to be constructive in terms of comments. It seems that most people think critiques are only for positive comments and have a hard time making suggestions. This is a skill that gets better with time as people get to know each other.
4. Adjust assignments based on comments.
I reuse assignments that work well and that I think have great lessons in them, but will change in the next class after seeing the results. Sometimes, students don't get as much out of them as I did.
5. Hands-on exercises work well sometimes, but have to be adjusted sometimes as the attention span and technology changes.
This has been the hardest lesson for me to learn. I learned almost all design by hand which I still think is amazingly valuable to understand the fundamentals, especially typography. It teaches you to train your eyes and I still think the computer is a tool, not the design. That comes from your ideas. But, I have had to adjust to get an assignment at all because younger students will push back to use the computer. Sometimes, it is the lesser of two evils.

All in all, depending on the age group and the class, teaching adjusts every week. I am surprised and challenged all the time. Good lessons for me and hopefully my students.