Five Steps to Freelancing “Full Time”

If you’ve been freelancing on the side for a while and are thinking of taking the leap into a legit sole proprietorship, here are 5 things I did that can work for you.

1. Define Your Values

“People don’t buy what you do, they buy WHY you do it.”
Simon Sinek

I’ve quit a lot of jobs in my career. Some jobs I outgrew, some were not a great fit, some just made me feel badly about how I was spending my time. For me, work without passion is a waste of time. I’m not saying I get lit up when I pay my insurance or schedule meetings, but part of what makes me a good employee and consultant is that I sincerely LOVE talking tech and solving problems. The type of problems that I get excited about have changed and will continue to evolve, but I will always seek out new and interesting tasks. Since my job title and roles will evolve, I need something to keep me steady at my core. That’s when I started to do some research into personal and company values.

People talk a lot about the vision a CEO has and how it shapes her company. To start my consultancy (regardless of how big it gets) I need to know what I stand for, what motivates my decisions, and how I distinguish myself from my competitors. I thought a lot about the best jobs and projects I’ve had and what made them great, what I choose to do with my spare time and money, and (rather darkly) what I want said in my eulogy. I developed these values, phrased as actions, to represent my highest priorities and deeply held driving forces.

  1. Have fun and delight in (most) everything.
  2. Grit gets it done. Get up and try again.
  3. Recharge and reflect often.
  4. Teach and learn continuously.
  5. Communicate openly and honestly.
  6. Design simple and elegant solutions.

2. Get the Books in Order

For many years I’ve freelanced on the side and filed a Schedule C for my profits. I withheld more taxes from my regular paycheck to cover taxes on my earnings and reinvested profits back into the my freelancing business. Now that I don’t have a day job that won’t work. After a bit of fumbling, I opened a free online business account with Small Business Bank. I use mobile check deposits and PayPal to take money in and I transfer money into my personal account to pay myself.

I  signed up for Harvest to manage my time and invoices (I got the paid version once demand required it). I usually bid jobs “fixed fee” but I track hours to check that my bids are accurate. I also took the plunge and pay for QuickBooks, primarily to calculate estimated taxes. I have yet to need PM software since it’s still just me (and I like it that way). Lastly, I’ve almost transferred all of my 401k accounts into a SEP-IRA and can make online check deposits to my kids 529 education savings plans.

3. Perfect Your Pitch

I like to do, and have done, a lot of different things. While I was reflecting on my values I thought long and hard about the kind of work I want to do and who I want to work for. Oddly  this is more of a list of project topics I DON’T want to take on, such as:

  • Religious or political organizations,
  • fast food, junk food, or soda (If I don’t eat it, I’m not going to help sell it), and
  • any topic I can’t share with my kids or my parents.

There are tasks where I dabble but would much rather hire out to a specialist. Tasks like:

  • front end development,
  • custom programming,
  • video or motion graphics, and
  • photography / photo retouching.

This leaves me with something way more specific to preach about when I get into a professional networking situation.  I customize my pitch for the situation, but I know what I bring to the table and what I’m really good at. Here’s what I do…

“I help organizations discover and define the problems their website needs to solve, then I help them find the right vendor to build it. Sometimes I build it or manage the project myself.”

4. Shout It Out!

Working alone is, uh, can be, lonely. It pays to have some practice with remote working and a fair dose of discipline. If you thrive in an office, there are a ton of coworking spaces in town. I have a basic membership to Capsity and I really like it. It’s close to my house, the people are great, the coffee is good, they have a lot of events I can attend (to get out of my bubble), and I have a place to meet clients.

You’re gonna need a network of local  and online support. I’ve spent years building a community of people I can partner with, ask questions of, and swap referrals with. Here are some ways to build your network:

  • LinkedIn: Get your profile up to date and fancy. I got some great tips from former Director of Recruiting, Paul Clark on how to write a good resume, essentially, “You get one page, tell me how you can help my company and show how you’ve done it before.” Brilliant advice, worked right away. Trade some recommendations for credibility, join groups that interest you, and follow companies whose work you admire. Link with everyone you know and look at profiles of those you admire… those folks will see you are looking and might want to connect.
  • Meetup: Get out of the house! Seriously. I aim for 2-4 outings a month, whether it’s an actual meetup group, lunch with a colleague or friend, a class or lecture, or a conference. Coworking spaces have regular networking events. Lanyard is an ok site for finding conferences. Use twitter to keep track of who is on the move too. I also started a Lean In style networking group via Mighty Bell and I keep a few groups on Facebook for particular interests.
  • Volunteer: I joined Catch a Fire to keep busy while I was getting going. For many, busy begets busy. The folks who you give good work away to become your loudest cheerleaders. But a word of caution, pro bono work is still work, and should be scoped and managed just the same. Be clear to your client how many hours you will put in, what’s included and what’s not. Consider billing your pro bono client and zero out the total so it is very clear the value you provide.
  • Tell Everyone: You never know who knows your next client! Tell everyone that you are freelancing and looking for exciting projects. Be sure your website up to date with your resume and skills and have business cards on you at all times. Blog about what you do and the successes you’ve had. Call up folks you’ve worked with, friends, and loose connections and have coffee or lunch. Find out what they are doing and if they have any leads.
  • Give Back: If you are a fan WordPress, like me, there are many ways to give back to the community. Getting your name out there, working with others in the WordPress community will build your reputation and increase referrals and partnerships.

5. Guide & Provide Solutions

I’ve read some articles that have solidified a change in how I think about my work. Previously, I would ask my clients what they wanted to do, now I tell them what they should do. This may sound bossy or presumptuous, but really it’s what you want from a professional when you have a problem. If I’m contacting a potential client for the first time I use some form of:

“I’ve heard you have this problem. I can solve it as I’ve done for these other clients. If you are interested in my help, I’m available to discuss at this time or this other time. Otherwise, be well and good luck.”

This approach has worked very well. I’ve extended it to most areas of my work. I still listen to their problem, their pains, their culture, the intricacies of the challenges they have been suffering for months or years…  based on their input I reiterate concisely what the problems are, how I’ll fix them, what they need to do, and when we’ll make it happen.

In my work helping organizations solicit proposals from vendors I’ve seen again how this approach wins business. The firms who get called back concisely reiterate the problem and describe how they will fix it. The best ones offer a solution for a problem the client didn’t realize they had. It’s tough to do this well, but when it happens it gorgeous!

Rocking It!

These methods have allowed me to thrive. Success for me is working when I want, for people I like, on projects that I find interesting. Having my own business lets me arrange my schedule to follow my passions, both paid and unpaid. I hope these tips help you.

Presentation Version for June 2015 Sacramento Meetup Group


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