11 Things I Learned From Freelancer to Agency Owner


I’ve spent the last 10+ years freelancing and bouncing back through different agencies. While there were plenty of perks both working for yourself and in an agency atmosphere, It always felt like something was missing. From the first day I opened up Photoshop and built my first website at the age of 13, I knew what I wanted to do for a living. From then on I dreamt about owning my own design agency.

For a long time I thought freelancing was good enough to satisfy my craving. Technically I “owned my own business”. However, I could never grow my freelancing business past a certain point, and always wondered how great it would be to collaborate in a team environment.

So I tried the agency lifestyle. I had great co-workers, had a lot of fun, and ended up managing my department fairly quickly. However, no matter how high I climbed I was working for someone else and always wanted to have a say and voice my opinion on how things were run.

I have since left all of that behind. I have fulfilled my life long dream. In January 2011 I co-founded Falling Up Media. It has been a very fun, crazy, scary and successful year for us. Most importantly I have learned more in the past year than I have in the past 10 years! Hopefully many of you have similar aspirations and goals and can learn a few of the things I have learned in the past year:

1. Do Not Undersell Yourself

As a freelancer you often jump on every job you can find, no matter how much it pays. At least I know that I did, I had to! Clients will often come to you as a freelancer expecting some sort of “deal”. Its sad that it works this way because we all know your work is worth more as a freelancer than most value it at. Getting out of the habit of underselling ourselves was the best thing our agency did! We struggled with this for the first few months and it was tough to make ends meet with rent, bills and employees to pay.

Know what your value is, and stick too it! You will be quite surprised when you raise your prices how clients will react, show the value in your work and reassure the client this can be the best investment their business can make. Outside of non-profit, we absolutely give zero deals on any project – that is just how business works and you must get over this to survive. You couldn’t walk into your clients store and ask them to lower their prices could you?

The truth is that you will naturally work harder to add more value to every client when there is more skin in the game. Clients appreciate you more, and you will appreciate them more. Once you look at pricing with a magnifying glass and determine the accurate amount of time you spend on a project, most of the time you will be shocked at exactly how much you are undercutting yourself.

None of us want to work for free. Provide valuable work for valuable pay and be proud of what you bring to the table. Don’t feel ashamed at how much you charge.

2. Specialize In Something

Find your speciality and let everyone know that you are the best at what you do. We started out as a standard web design shop who did a little bit of internet marketing. We gained business and things were going well.

However, for some reason we never attracted the kind of business we were hoping for. Having been around WordPress since its creation, both my partner and I knew the ins and outs of it as good as anyone else in the field, and we are great at SEO.

We are proud of what we do and work hard every day to get better because it is our passion. We obviously knew these were our strong suites from the beginning, but when we started advertising and selling ourselves as WordPress and SEO specialists, we started attracting better paying clients with great projects that we loved to work on!

We still provide all other services our clients need of course. However, we make sure to put the right talents and people in place who are passionate about what they specialize in. Make sure you put your company in the position to attract the type of work that you want.

3. Work With Other Agencies

Our business blew up when we started working with other agencies. Remember that not every agency has the capabilities that you have, and you don’t always have the capabilities that other agencies may possess.

Stop thinking of them as competitors and start looking at them as opportunities and partnerships. Find a few local agencies who you think may be lacking in areas that you excel in and reach out to them. Don’t sell yourself in the first email, let them know that you really like their work and you would love to sit down with them and talk about how you can work together.

40% of our work comes from other agencies, and we love working with them as partners. You have to put some effort into relationship building, but its been well worth it for us!

4. Work On Your Business, Not In Your Business

Its very easy to get consumed in working in your business, but you must step back and start working on your business! We went through most of 2011 working in our business, until we met an awesome business coach! Our coach taught us that we must continue to work on our business and treat our business as a client by finding time to work on our projects.

But most importantly he taught us that we constantly need to work on monthly, quarterly, and yearly goals. These goals can be personal, professional, financial, or whatever you particular feel is right for your situation. But most importantly you need to make a plan on how you can obtain that goal, and follow through.

For example, one of our goals for 2012 was to increase our annual revenue by 60% by the end of 2012. We are well on our way to exceeding that goal because we made a plan to work on our business instead of in our business.

We set daily tasks, monthly milestones, and made sure that we are constantly evolving and getting better. When you focus on your plan and keep your goals in sight you will be determined to make them reality.

5. Find A Great Partner

My partner is amazing and our business couldn’t survive without him! Its great to talk over anything and everything to make conscious business decisions. I’ve read on almost every business book I have seen: Absolutely do not go into business with a friend. I am sorry, but I call BS on that!

We grew up together in the same small town, played little league together and went through high school together. While we were not the “BFF’s”, we do enjoy each others company, have an understanding of our personalities, and have ABSOLUTE TRUST in each other, and I think that is something you cant just stumble across. Finding a great business partner is going to help your business grow, while taking some of the day to day stresses off of you.

6. Have Solid Contracts

Luckily for us we have yet to come across a contract dispute. I would like to think its because we try to go the extra mile for every client, but it could be because we have a solid contract.

In every project proposal we very clearly outline every item of work that will be completed, what we will do, what we will not to, how long we will do it for, and what it will cost. Of course its much more detailed and in depth then that, but you get the idea! You can find contract outlines floating around the internet, but I would recommend having a lawyer draft one up for about $200-$500.

7. Build In Retainer Pricing

Any agency in our field should have at least one retainer service they provide. Sure, the huge one time projects can be nice, but there is no better feeling than at the first of the month you know you have $X,XXXs coming in automatically, and your bills are paid! We sell a lot of SEO & Social Media on monthly retainers, usually on 12 month contracts which provides great peace of mind for all of us.

Retainers also help you to be involved with your clients and their goals, and help you constantly learn and strive to add value together. It creates a working relationship between you and the client, and if you seek to add value to each one, also manifests into a lasting business bond.

What if you don’t provide SEO or marketing services? A few options you can consider are setting up a reseller plan and charge for monthly hosting, or coming up with some creative monthly website update package you can sell your clients. Even if its just a couple hundred bucks it all adds up quickly!

8. Stay On Top Of Project Management

As a freelancer, I was often just working with a few clients at a time, most of which were straight forward projects that I could easily manage through email, notes, or even memory (Yikes!). As our agency started gaining speed, I quickly realized that I just couldn’t remember everything!

The worst thing you want to do is drop the ball on a project, this makes you and your company look bad. You cant stay in business without a good project management system where you can easily separate, delegate and organize your tasks and priorities. This also is a good practice to keep your team in good communication. Remember you are not by yourself any more! You should always be thinking about your team and surrounding yourselves with good communication practices.

We struggled finding the right project management system for months, we looked at a number of free and paid options including Active Collab, Apollo, and Basecamp. We decided on Basecamp, its by far the easiest to use and has iCal integration, its relatively cheap, and integrates with a number of add-ons.

Aside from being an overall project management superhero, Basecamp is great to track your employee’s hours and completed work. I would highly suggest checking out Basecamp and the whole 37 signals suite.

9. Attend Conferences & Create Relationships

Days after we received our official LLC papers back from the state, we attended a WordCamp conference. We literally went to the conference as a brand new business with zero clients and we left with 5 soon-to-be clients, two of which are big names and have given us consistent work over the last year. We didn’t sell anyone, we just went to genuinely learn and meet people. For about $100 we were able to expand out knowledge and create valuable personal and business relationships.

Some industry related conferences are outrageously priced, and you often have to travel and pay for lodging and food. I suggest checking out a local WordCamp near you! WordCamp’s are usually around that $50 per person range. The atmosphere is always awesome and the amount of connections you can make is extremely valuable.

If you are looking to make a real impact, consider speaking at a conference. You will not only get in for free but you have the opportunity to set your business above the rest as a leader in your field. Speaking at a conference can also benefit your SEO, most conference websites have high domain authority and offer a link to all of the speakers websites.

10. Find A Mentor

Assuming most of the readers of this post are young professionals who are wanting to transform their freelance business into a serious agency, find a mentor! Both my partner and I thought we had it all figured out. We were closing deals, creating great work and getting paid. Then we met a couple of “mentors”.

When we met Pete, our business coach and Park, the owner of large agency here in town, we quickly realized how much we didn’t know about the business side of things! Since meeting Pete and Park, we have changed our whole perspective on business and have opened our eyes to opportunities we never knew existed.

Just by building relationships with other professionals, we are now on the receiving end of priceless insights and knowledge and our business is growing as a direct correlation of these mentor relationships.

11. Stay Ahead Of The Game And Never Be Afraid

Steve Jobs once said “I think we’re having fun. I think our customers really like our products. And we’re always trying to do better“. His quote is the mentality that every business owner should strive for, especially in our industry!

In our digital world you must love what you do and have fun every day you come to the office, that passion will naturally translate into your work. Right now, you are likely reading Speckyboy Design Magazine because you want to learn. Take your willingness to learn new things and encourage your employees to do the same, and you will be just fine.

Learn From My Experiences

I wouldn’t call any of these “mistakes”, rather just a natural learning curve. Learn from my experiences and it will make your transition from freelancer to agency owner much easier! There may be a lot of agencies popping up all over the place, but there is still plenty of room for any company who does quality work.

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