The Freelance Primer

Published on: August 29, 2012 |Tags: ,,, | Categories: Articles

I gave an hour and twenty minute talk at How Design Live / Creative Freelance Conference in Boston on the art of the start. This talk has some serious meat on its bones. The organizers were kind enough to provide me the audio and I then paired it with the slides to create a video to share. We always give our educational content away for free to our audience and this isn’t going to be any different.

I started freelancing full time out of necessity during the dot bomb in 2001. There were no blogs on freelancing, no conferences, but I was deeply blessed to find a mentor who helped me avoid the worst mistakes my first year. While you shouldn’t get paralysis by analysis (just get started), certain key tips often make the difference between navigating a successful freelance career and a lot of sleepless nights. Whether you are dreaming about freelancing or in the thick of bootstrapping, be practical and be intentional about running a business and you will be successful.

  • Why you ALWAYS get a deposit
  • What to spend money on and what to skip
  • How to get a business license and what form of business to choose
  • Don’t be a cowboy, get input from the right people
  • Why you should clock your time, even if your aren’t paid for it
  • Contracts matter – finding a template you can use
  • The IRS is watching: separate bank accounts and track your finances
  • Planing makes you real money: think about deductions and expenses now
  • Avoid the bad projects and evil clients with a project checklist
  • 6 months in the bank = freedom to define your terms
  • And so much more…

Watch The Video Now

Although the video was previously only available to those who’d signed up to receive the Tribesterly email digest we’ve been working on, it’s now public and accessible to everyone. Check it out:

Some supplemental resources can be found below, too.

With The Right Setup, Anyone Can Kick Ass

I included the table of contents for the talk below as well as a small additional set of thoughts on the biggest mistakes freelancers make. Hope you enjoy.

You might also want to check out other articles & videos we have on the topic of freelancing (there are tons more beyond these):

The Why
The Vehicle
The 6 Fs
My Dreams List

The Setup
Business Type
Biz License & other paperwork
Professionals pay off
Your up-front costs
The IRS is watching: separate bank accounts / cc
Track your finances: Quickbooks, Quicken, Freshbooks …
You MUST pay taxes
What can you deduct?
#1 goal: 6 months in the bank

The Patterns
Daily Habits
Work Comfortably
Home Vs Coworking Vs ?
Clock all your time
The Calendar
The Daily minimum
The Urgent Vs The Important
Balancing the Fs
Back your shit up

Finding Your Customers
Make a list – contact everyone
The perfect voicemail
Marketing – website, portfolio etc
The project checklist
Sell when you need it least
Fixed Vs Hourly
Managing your load
Experiment with your rate: Supply & Demand
My income per year
“Do Good Work & Tell People About It”

Working With Customers
How do we win?
1 out of 3: why they fail
Management Slides

bonus thoughts for this post:
(not in the video as I had to cut it due to time):

Most Common Mistakes
Not clocking
Taking on too much
Waiting to sell until you need it
Failing to experimenting with your rate
Forgetting to save for taxes or tracking expenses
Setting expectations poorly
Pretending to be what you are not (an agency)
Wasting money on the wrong things
Not getting the legal biz basic in place (but not obsessing about them)
Allowing the urgent to trump the important
Going with the torrent rather than creating a pattern to live and work by
Not having a backup in place
Working without a contract (or neglecting to read it)
Not getting paid a deposit up front
Finding out how to win a project after you have it

8 Responses to The Freelance Primer

  1. Adam Kayce says

    Excellent presentation, Shane – thank you so much for posting it. I’ve been freelancing full-time for ~6 years, and I still got a lot out of it.

    One question that I haven’t been able to find an answer to: When you say, “clock your time”, do you have a certain (software) solution for that? I clock all of my billable time already (I use, but what about the in-betweens? Do you have details anywhere of what kinds of things you track, notes you make to help you make sense of it all, etc?

    Thanks again!

  2. Shane Pearlman says

    Hey Adam,

    I’ve clocked my time to a variety of solutions over the years. Currently it is built in to our project management system. We track time by activity type ( and then assign a billable status to the activity per project. It is not as granular as marking each item billable or unbillable, but it is easier and works well enough once you get to be a team (when people don’t always know what is / isn’t billable).

    My clocking methodology is ever evolving. I’ll admit to having a personal challenge with clocking the last few years do to being in a primary management/ sales / product manager role. I rapidly context switch so much that clocking is tough. Ultimately though it is a matter of discipline + forensic clocking. At the end of every day I compare my my time clocked to my calendar. If it is off, I try to figure out what I missed. I have a few general catch all type tasks in operations, finance, sales etc that I clock to a lot ( with notes.

    The goal at the end of the day is to be accountable with the value of my time. Since in our crew, manager time is currently our largest bottle neck, being efficient with it is extremely important. The same is true for a freelancer.

  3. Adam Kayce says

    Awesome – thanks for that. Definitely gets the ol’ noggin thinking of how to best make it work… but I can already see how to integrate it into the system I use now. And thanks for the visuals; most helpful!

    Have you ever seen the <a href=""lego time-tracking method? It looks like it’d be more seamless on the front end, but transferring it to a digital medium for long-term tracking does seem a bit impractical. (Bummer, too; the kid in me likes the idea of legos on my desk…)

    Yep – accountability is the key. The last time I tried tracking everything I did in the day, my lag time between projects sure tightened up. Thanks again.

  4. Pingback: Website Relaunch + a Freelance Primer

  5. Pingback: Muse-y Motivation (Part II)

  6. Chris Ames says

    You had me at Pinky Pie.

  7. Pingback: My Motivation for Becoming a Freelancer by Modern Muse Design