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How I Grew My Freelance Business: 7 Tips To Becoming A Successful freelancer

How I Grew My Freelance Business: 7 Tips To Becoming A Successful freelancer


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I started my Freelance business back in 2017, with my first client, Shannon with Shannon’s Ageless Fitness. (Technically, my first client was back in 2014 but I had no idea what I was doing so I don’t like to talk about that. I really do feel sorry for that client.)

I’ve learned a LOT over the last few years, and I’m excited to share with you my experience, and my 7 tips for being a successful freelancer.

But first, some backstory.

Before freelancing, I was all over the place. I started my adult vocational journey in the Navy basically right out of High School. In the Navy I learned a bunch of useless crap about Nuclear power, physics, chemistry etc. Luckily I also learned a good amount of useful information regarding electronics. Upon leaving the Navy, I put that electronics knowledge to use working as an Electronics Technician for Collins Aerospace (then Rockwell Collins) and later for Trapeze.

After about 4 years doing that I finally admitted to myself that while being an Electronics Technician paid pretty well, I just didn’t like it. In fact, I've tried a lot of different things that I didn’t like. I’ve worked for GoDaddy helping people with enterprise email and SSL certificates, I’ve sold life insurance, worked in a Procter & Gamble factory, I was an electrical apprentice for 6 months before accepting the job at Collins, just to name a few.

Then, in 2017 something happened that would change my life.

I was turned down for a job.

Not just any job, this was the perfect job. I did everything right (The CEO even told me once that while he wasn’t in charge of hiring, he thought I was doing everything right). I spent about 6 months courting this company. I’ve never wanted a job more than I wanted this one. The company was cool, the people were great and the job itself sounded fantastic. I made it all the way through their interview process, and I thought everything had gone really well and I was convinced I would be offered the job.

I was not offered the job.

This also came after having been laid off from the one job I ever had that I actually enjoyed.

When I got the email that I was not being offered the job I was angry. Like, REALLY angry. I couldn’t believe it. I did everything I was supposed to. I had been courting this company for 6 months, I got to know people that worked there and I really felt like we got along and that I would be a good fit culturally. I also felt like I was a great fit for the job itself. How could they not offer me the job? What were they thinking?

Of course, I eventually calmed down and began to think rationally again. I harbor no hard feelings towards this company. I know the hiring process must be really difficult and with as awesome as that company is, I’m sure they had a ton of super great, highly qualified people applying. I still enjoy following them and their progress as they (rapidly) grow and evolve. I even make it down to Iowa City occasionally for some of their tech talks.

But initially I was really angry. And not just angry, I was also overcome with an overwhelming feeling of despair. Here I was, in my early 30s and I had no idea what I wanted to do with my life. I’d worked in just about every possible industry I could and hadn’t found anything that felt right. I felt like this company was my last chance at being happy, and that their rejection meant I was doomed to a life of working jobs I hate just to pay bills and retire on a meager stipend and die miserable, having done nothing special with my life.

That might all sound super dramatic but after years of working jobs I didn’t like, wondering if there was anything out there for me, it was really starting to wear on me mentally. I was staring down 30 more years of going from job to job, never really fitting in anywhere, never enjoying my work, always dreading Mondays, living for the weekend...

At the time of the Great Rejection, I was working as a subcontractor for a friend of mine. It was good work, I had a skill for it, but I kind of hated it. The pay was fair, but there were no benefits. The best thing about it was the flexibility. My wife was going to school, so I had to take our girls to school and pick them up so a traditional 9-5 wasn’t going to work very well. Had I not been rejected for that job we would have probably ended up spending a good amount of money on a day care service that would take the girls to and pick them up from school. So I had the flexibility I wanted, but I was so sick of working in construction. My friend is a great person to work for/with, and I’m super grateful for the opportunity to be able to support my family during that time, but I wanted out. And this job was supposed to be my ticket out.

I was so upset when I got the rejection email that I couldn’t even bring myself to go back to work as a subcontractor at first. I literally just couldn’t.

I was so depressed I actually gave Uber/Lyft a shot. I did that for probably a month, and then I found a job as a web developer for a small company out of Iowa City. This job paid exactly the same as subcontracting, but I got to do something I enjoyed in a climate controlled office. No more killing my body, working out in the elements.

This job ended up not working out. (big surprise). I just wasn’t getting enough hours and it was becoming increasingly not worth it to me to drive all the way to IC (about 30 minutes away) for an hour or two of busy-work and then drive home. And when I say busywork, I mean busywork. At one point he had me installing shelves in the basement, and one day I helped him pack his son’s stuff up in a moving van. He was paying me to do these things because he didn’t have any web development work for me.

So eventually I gave up and went back to my friend to work as a subcontractor. But by this time I had made an important decision: I was going to work for myself one day. Working for a company was clearly just not going to work out for me. I needed to be my own boss, work on my own terms, do what I love. I’m like Steve Jobs without the intelligence and knack for design.

Basically I wanted to work on my own dreams, not someone else’s.

So I decided for the first time that I was going to take the idea of making money as a web developer seriously. I had the advantage of having a job that was flexible and would pay the bills while I worked on my business. This was a double edged sword however, as it’s hard to work on your own business when so much of your time is taken up with a job. I was also super exhausted after work every day which made it hard to stay motivated and hustle.

Eventually I started taking 1 day off every week from construction. This day became my meeting day. Any time someone actually wanted to schedule a meeting with me, it had to be Wednesday, because that was the only day I had off. This was my first step towards prioritizing my business, even if it was just one day a week.

My first real business goal was to free myself of working in construction before winter of 2018. I did not like working in construction, and I REALLY didn’t like doing it in the winter. For a lot of reasons.

1. I’m a total mamby pamby, but my friend/boss was not. He had no problem building a deck in 10 degree weather. I had lots of problems with that.

2. I have two vehicles. A 2011 Taurus that is the absolute WORST winter car ever. I would get stuck all the time because the tires literally get 0 traction on the slightest bit of precipitation. The other is an F150 that gets around GREAT in all sorts of weather. That beast never gets stuck, but it has no heat!

A couple things happened that really helped me out during this time. First, my wife finished her schooling and actually got a good job fairly quickly after having graduated. This took a lot of pressure off of me to provide. I was also starting to gain a small amount of traction with my own business.

I’m happy to say that I reached my first business goal! I started by taking one day off a week, which eventually turned into 3 days a week off, and before winter came I was able to tell my friend thanks for everything but I’M OUT.

Again, this would not be possible without the hard work my wife put into going back to school to become an Occupational Therapy Assistant. I honestly don’t know where I’d be with my business if it wasn’t for her.

But I did it. I got a few clients, made some connections, and was able to actually make a small amount of money and avoid working construction in the winter.

And it’s only gotten better from there. To give you some perspective, I went into my bookkeeping software to look at where I’m at this year compared to last year.

A lot of people don’t feel comfortable talking about money, especially income but I don’t care so I’m going to share these numbers with you:

In 2018 I made $8,665. That’s not counting my work as a sub-contractor or working for the web development company in Iowa City. That’s just my business. That’s not a lot of money, but it was my first year in business and it was mostly profit.

It’s early August, 2019 and so far this year I’ve made $14,994.89.

Again, that’s not a ton of money but it’s a lot more than last year. That puts me on track to make about $26,000 for the year, with almost no overhead. That’s a pretty good 2nd year I think. This also doesn’t take into account a client I JUST landed that told me they are budgeting about $2-3000 of work for me every month. That would put me at about $36,000 for the year, which would be about a 400% increase from year 1 to year 2.

Needless to say, I’m very excited to see what 2020 looks like.

So how did I do it? Or rather, since I’m not exactly where I want to be quite yet, how am I doing it? Here are my 7 tips for being a successful freelancer.

1. Whatever it takes.

First of all, you really need to have a “whatever it takes” kind of attitude. If you have to work full time in a job you hate just to pay bills while you try to build your business on the side, then you do it.

If you have to give up some part of your lifestyle that you simply can’t afford anymore right now while you work on your business, then you do it. What’s more important, drinking a latte every day now, or being able to travel to Italy and have the best latte of your life 5 years from now?

2. Be smart.

Like I said I was pretty lucky that my wife had a good job and I wasn’t solely responsible for supporting our family. It allowed me to focus more on my business and less on working construction. However, you might not have that luxury, and I get that. You might need to consider making some sacrifices, and saving every penny you can until you have 6-8 months of expenses saved up and then quit your full time job and maybe even keep working part-time just for a little added financial security to focus more on your business. And even though my wife had a good job, she wasn’t making a million dollars. I still need to contribute and I want to contribute, which is why I didn’t just quite construction right away.

I do NOT recommend just quitting your job to strike out on our own as a freelancer with no savings built up and no guaranteed client base. Unless you’re single and OK with living in a van down by the river, that’s probably not a great strategy.

Another luxury that some people have is that one initial client. I know a gal who left her job, and her first client as a freelancer was her former employer. Not everybody will have that. Whatever your current situation, be smart. Especially if you have a family that depends on you. They have to come first. Hopefully, your family will be willing to come along-side you, and make some sacrifices of their own (mine sure did. My wife worked part-time at Starbucks while she was going to school full time) to help you focus on building your business.

3. Networking, networking, NETWORKING.

Networking is a slow game, but it’s super important for any aspiring freelancer and probably any kind of business owner. Especially if you rely in any way on business from people local to you. I went to my first networking event in September of 2017. It was an open coffee meetup at Roasters in the NewBo Market. I made my first connection that very day. Her name is Rina Jensen and she’s a business resiliency coach. This would be the first of many connections made at many networking events. I also connected with Joshua McNary of McNary Marketing & Design who I ended up doing some work for later on. The payoff from networking is very rarely quick. It’s not likely that you’ll run into someone at a networking event and sign them on as a new client a week later. But it’s SUPER important to meet as many people as you can, and build REAL relationships with them. The client I mentioned that’s ready to pay me $2-3000 per month? They told me I was highly recommended to them by two different people. Those two people were never even a client of mine! They are people I met through various networking opportunities, and built a real relationship with. I’ve known them for probably 2 years and because of this, I’ve landed a seriously great, very lucrative client.

Two years! Talk about the slow game. But it’s worth it.

I mentioned I met McNary and formed a relationship with them. I had the opportunity to build a website for a pretty big company here in Iowa called Americlean Iowa. Where did that opportunity come from? Joshua McNary referred me!

I can’t stress enough the importance of networking. It’s taken me probably close to two years to get to where I am today, but it’s important to know that I don’t do any paid advertising. I don’t run Google ads or Facebook ads. I’m not promoting posts on LinkedIn. The only “paid advertising” I do is my business cards. This is somewhat a point of pride for me, but it’s mostly out of necessity. I just haven’t really had any money left over that I felt comfortable putting into ads. Especially since I’m not a marketing expert and was afraid I’d just end up wasting the money with ineffective marketing.

So get out there and network. Network your butt off. But don’t be weird about it. You don’t want to walk into a networking event and just start throwing you business card in people’s faces. You want to actually meet people, listen to them and learn about them. You will have plenty of opportunity to talk about yourself and your business, don’t force it. You need to form real relationships with these people.

Again, you need to be smart about it. I don’t mean to be rude, but there are people that you want relationships with, and some that you don’t. I know that sounds harsh but it’s true. While you should be trying to meet as many people as you can and forming real relationships with people, you don’t need to form relationships with EVERY single person you meet. You’ll start to see which people tend to show up at all the networking events and are invested in their business and the business community, you’ll also start to see which events are worth your time and which aren’t. I’ve been to several networking events where I decided after one or two visits that it just wasn’t worth my time. But again, try to remember that the fruits of networking are rarely instantaneous so don’t get frustrated when you start networking and the clients don’t start rolling in.

My advice regarding networking is to just have fun with it. Enjoy yourself. Make friends. If you do good work, and you embed yourself in the small business/entrepreneurial community, business will come. And even if it doesn’t work out, you’ll at least have made some friends along the way.

4. Collaboration.

Speaking of relationships, there’s one kind of relationship that you need to seek out. Try to find people who do similar work as you, and see if there’s any opportunity for collaboration, or referral reciprocation. You absolutely can’t go into this being super competitive with other people doing the same thing. I have formed great relationships with several people in the Corridor that offer the same services I do. And instead of being super stand off-ish, I’ve built relationships with these people and it’s been nothing but beneficial for all of us. Apart from actual collaboration and referrals, you can also benefit by learning from each other. While you might do similar or even the same thing, you both likely know things and have experienced things that the other hasn’t, and you can both benefit from a real relationship.

5. Branding.

Let’s talk about branding for a second. I certainly don’t claim to be any kind of expert on branding, but I’ve seen a lot of interesting things this last couple of years while networking and watching so many other entrepreneurs and business owners grow and evolve. I’ve also learned a lot watching my own brand evolve over the years. My “official” brand is Cedar Rapids Web Design. I have a simple logo, involving a C and an R in the Cardo font. But when you ask people around Cedar Rapids to describe my brand, there’s about a 1% chance they’ll talk about that logo or even my website or business name.

There’s a 100% chance that they’re going to bring up my hat.

Yes my hat.

A couple Christmas’ ago, my mom bought me a brightly colored Google branded beanie because I’m a total Google nerd. I wore the hat a lot, because it was winter, and it’s a very bright hat, and I’m tall so it really sticks out. Spring came around, it started getting warmer, and I showed up to something without the hat, and a ton of people kept making jokes “hey man where’s the hat?” or “hello sir are you new here? Oh I didn’t recognize you without the hat”.

Some of them have even started calling me the “Google Hat Guy” (*ahem* Rina Jensen).

So instead of fighting this and trying really hard to push my CR Web Design logo/branding I just went with it. My business cards don’t even have my business logo on them, instead they have a vectorized image of my face with the hat (the same one you see in the upper-left corner of this website).

Personal branding is important, especially for a freelancer. When you’re a freelancer, you ARE the business. People are doing business with YOU, not some vague entity made up of 30 people, 3 of whom actually give a damn about the agency. They’re doing business with YOU, they’re hiring YOU, and they’re trusting YOU with their success. Your personal brand is important, and it should be natural. I had no intention of becoming the Google Hat Guy, it just happened. It was just who I am.

You also need to consider how you’re presenting yourself. For the longest time, whenever people asked me that networking question “so what do you do?” I answered like this: “Well right now I’m working in construction part time while I work on my web design business”. One day, thanks to an incredible workshop on Elevator Pitches led by Jennie Morton, owner of Herringbone Freelance it occured to me that I was being an idiot. I was basically just telling everybody I met that I wasn’t really legit yet, and that I wasn’t taking my business seriously. People heard me answer that way and they probably thought “well he won’t be around long”.

Not smart.

Once I had this epiphany, I stopped mentioning construction altogether, and started answering like this “I’m a freelance web developer” and left it at that. People don’t need to know that I was working part time in construction. It’s not important to them or even me. They need to know that I’m a web developer, and if you need a website built for your business you should come talk to me. I don’t need people calling me because they want their bathroom remodeled.

6. Know your worth.

I’m not talking about your worth as a human being, though that’s important as well, I mean know what you as a business owner are worth, and stop charging less than that. There are a lot of opinions floating around out there about doing free or cheap work. I tend to lean towards “DON’T DO IT!” but I also understand that sometimes it does makes sense.

When I first started and built my very own (ugly as hell) website for myself, my portfolio consisted of about 4 or 5 websites that I had built for myself. I didn’t even have any client work to display yet. So maybe in the very, very beginning it might make sense to do some free work just to build your portfolio. But honestly no matter how broke people say they are they can usually afford SOMETHING. I would encourage you, instead of doing free work to try at least get something for the project. It might be a $2000 project but you’re new, you’re trying to build your portfolio, and $500 is better than $0 so ask for $500. Don’t fall for the exposure trap. If they’re in a position to offer any kind of real exposure, they’re likely also in a position where they could afford to pay you. Something like 90% of startups fail. Keep this in mind when some exciting new startup promises to carry you with them to success.

Also, if you’re going to do free work, do it on your own terms. One thing I did very early on was offer a promotion for Iowa based non-profits. I started telling everybody that I was going to build a website for FREE for 1 Iowa based non-profit. Word got out and I had over a dozen non-profits apply. It doesn’t have to be anything fancy either. Offer to build a simple 3 page website for free for a non-profit and you will get people's attention. I know several established agencies that actually do this regularly and the recipients are very grateful.

I would also shy away from “hey if you [do your thing for me for free] I’ll [do my thing for you for free]” type conversations. In my experience these are almost always one-sided and it also puts people in an awkward position. I’ve had people offer me their services that I’m just not interested in. It’s awkward having to say “thanks for the service-swap opportunity but I don’t really want your product/service so...”. Or maybe I would be interested in their service but they’re offering me $200 worth of whatever they do in exchange for a $2000 website...

At the end of the day, doing free/cheap work can make sense at times, but you need to get away from doing free/cheap work as soon as possible. You definitely don’t want a reputation for being the cheapest option in town.

7. Be a sponge.

I mentioned being intentional with who you choose to build relationships with, and this is one reason why. You need to learn from people. You need to learn from people who are in your industry, you need to learn from people who are not in your industry. You need to learn from new business owners, old business owners. There’s no shortage of people out there that you can learn valuable lessons from regarding your particular trade, or business ownership in general. And also, don’t be stingy with what you’ve learned. Like I said before, collaboration > competition. There’s plenty of work out there for everybody, there’s no sense in burning bridges because of some competitive nature. Instead of competing with each other, we need to work together and learn from each other.

Over a year ago I started a Freelancer Meetup. We have a Facebook group, and we meet twice a month at a coworking space (coworking spaces are a great place to meet other freelancers, btw). It’s been fantastic! Several of the people who come to this meetup are web developers like me, many are not. We all enjoy the fellowship and learning from and teaching each other things. It’s honestly one of my favorite things about being a freelancer.

One thing I’ve noticed about freelancers, especially the ones that fail and end up going back to the corporate world is that they were good at what they did, they just didn’t know how to run a business. They didn’t understand lead generation, sales/marketing, invoicing, taxes, project/time management, bookkeeping etc. This freelancer meetup has been a fantastic resource for myself and others as we’ve had guest speakers and round table discussions about all the things we struggle with as freelance business owners.

Well there you have it. My 7 tips for becoming a successful freelancer. It feels a little weird for me to write a blog post about being a successful freelancer when I’m not even close to being where I want to be, but one thing I’ve realized of the last few years is that you’re never done. If you wait until you’ve “arrived” to tell your story and share your knowledge, you never will.

So hopefully I said something halfway useful during this blog post. I’d love to hear your thoughts on my 7 tips, and if you have any tips of your own I didn’t mention, let me know!