How to Win at Freelancing Without Killing Yourself

How do you describe freelancing? Do you consider yourself a freelancer? Want to become one?

The idea of freelancing can take my forms. It’s malleable like play-dough, which is a good thing! Why? Because it can be endlessly molded to fit your talents, experiences, passions, and pursuits.

But for all of its appeal, a freelancing lifestyle is not without its challenges, unknowns, danger zones, and derailers. Thus, to survive and thrive as an independent freelancer you need to up your game and play it smart.

And that’s precisely how the new Unconventional Guide to Freelancing can help!

The Unconventional Guide (UG) to Freelancing is the latest installment in the UG series. It has a simple mission – to enable you to grow your business without killing yourself. That sounds swell to me!

You probably know Chris Guillebeau, the lovable nonconformist behind all the UG products. But for the UG to Freelancing Chris has enlisted an equally crafty sidekick – Charlie Gilkey. You may not know Charlie, but you should, and I suppose now you do! Oh, and Charlie is actually the author of the UG to Freelancing.

An Exclusive Review of the Unconventional Guide to Freelancing – by Matt

I’ve read the 22,000+ word monster guide. I’ve listened to the 5 audio interviews with successful freelancers. And I’ve analyzed the (1) Agreements, Contracts, & Policies Checklist as well as the (2) Key Lessons + Recommended Resources guide (both bonuses!).

In a word – WOW!

But rather than leaving it at that rather inarticulate grunt, I thought I’d delve deeper and share my options on four fronts – general impressions, specific impressions, special insights and critiques.

Buckle up. This is going to get good!

General Impressions

Robustness was my immediate reaction when initially scanning the table-of-contents and skimming the material. Charlie didn’t leave many stones unturned about the world of freelance business. He plunges unabashed into the sexy commercial side of freelancing as well as the very unglamourous side of back office paperwork. And he doesn’t seem to play favorites with any particular facet (though I’ll venture a guess that he doesn’t enjoy taxes!).

Next, I was pleasantly surprised at how easy to read and understand the material was. I’m not a freelancing pro by any measure. Thus, I admit I had my concerns about how dense the material could be. Mind you, there’s a crap load of content! But thankfully it’s all very tasty and won’t give you indigestion.

Last general impression was the guides fantastic action-orientation. Each section contains specific, real-world-based action steps that you can (should) take now to immediately uplift your business. These action steps are complemented with thoughtful challenge questions too.

So, yes, you’ll need your thinking cap on for this, but you knew that already, right?!

Specific Impressions

I have to be very careful here because I could easily go on for about 22,000+ words of my own! So I’ll intentionally try to keep this brief. Here goes…

The UG to Freelancing is formulated around the four chief identities you have to assume (and balance) while building your freelancing business – COO, CMO, CFO, and CEO. The following snippets are my favorite learnings from each.

1. COO (Chief Operating Officer)

• “The limiting factor of your productivity is not usually time but your energy and attention.”
• “Avoidance is still an active process that takes some of your TEA” (time, energy, and attention).
• “You are your business – make time for yourself.”

2. CMO (Chief Marketing Officer)

• “Self-promotion is mandatory.”
• “Ask yourself the following question: with all the other options in the world, why should people work with you?”
• “Determine the top three benefits of working with you and hammer those home. Make them grounded in emotions.”

3. CFO (Chief Financial Officer)

• “It’s not what you make – it’s what you keep.”
• “The key difference is that an investment increases your resources in time, whereas an expense decreases your resources.”
• “Less feasting equals less famine.”

4. CEO (Chief Executive Officer)

• “The goal is to move from a one-to-one service model to a one-to-many model — which can be productizing our skills, experience, and perspectives or increasing the number of people we can serve at once.”
• “You are not a service provider – you are a solution provider.”
• “Hustling is not a sustainable business strategy.”

To me, the choice of architecting the information around these four chief identities was brilliant! It helps you visualize the role and responsibilities within each discipline. Further, it gives legitimacy to the words and allows you to emotionally connect with ideas. Double Woot!

Special Insights

I have two, and I’ll try to keep these brief too.

First, Charlie’s freelancing philosophy and tactics mirror beautifully with Agile software development. I’m quite familiar/experienced with Agile from another dimension of my life, and let’s just say I’m a fan!

Agile is predicated on maximizing throughput, focusing on “done”, and eliminating needless activities and waste. Agile embraces change, operates in iterations (cycles), and by nature is an empirical process. And Agile rewards delivery of value above all else, especially over illusions of control. All this flies in sharp contrast to traditional (waterfall) software development.

Those Agile hallmarks show through in Charlie’s recommendations for optimal freelancing. As he says, “think about growth in terms of additional capacity to deliver solutions and generate profit.” He also advocates producing small deliverables of value for clients that rapidly show progress.

Maybe Charlie and I share the same alter-universe!

Second, the UG to Freelancing instills a belief system akin to the “Why-First” mindset. The Why-First mindset (also called ‘The Golden Circle’) teaches that persuasive marketing, strong relationships, compelling storytelling, etc. originate not from “what” the subject matter is but “why” that subject matter is important.

The premise is simple – emotions trump logic! So, when building your clientele, marketing your services, or trying to captivate that cute girl or guy you just met, lead with your “why” (emotion-based benefits) and end with “what” (logic-based rationalizations).

This is a simple formula for world-changing results.

Note: Quick acknowledgement to Simon Sinek, http://www.startwithwhy.com/, father of The Golden Circle!

Critiques

Quite honestly there aren’t many legit critiques to give. I’m not just saying that because I’m friends with these guys, which I’m not by-the-way (we’ve only just met!).

So rather than inventing a list of critical hubbub, I’ll simply share my admittedly limited amount of suggestions. Note that these are not critiques in that they aren’t short-comings.

1. Learning more about freelancing variances from an international perspective would have been interesting. While I’m US based, it would have been intriguing to see how taxes, marketing, and strategy decisions vary (or not) from country-to-country and/or region-to-region.

2. Continuing on the international theme, how does the smart freelancer with clients in multiple foreign locales manage currency rates and exchanges? I imagine there’s a simple answer here – chose just one (e.g. USD). But I wonder how much geo-arbitrage goes on and whether there are any strategies and tactics to make it worthwhile (seems like a headache to me).

3. For the 5 interviews with successful freelancers, I (personally) would have preferred video. That’s just the way I operate; certainly others are different.

4. This one may be controversial. When do you know when to “close shop” – that what you’re doing just isn’t going to work? What are the warning signs – the red flags? How much time to you reasonably give your freelancing venture before you pull the plug? Hard questions I know, and I hope to never face them personally. But I’d rather be prepared for death than ignorant of it.

Hat-Tips and Kudos!

Hat-tips to Charlie, Chris, and all their freelancing co-conspirators who put so much passion and energy into creating this product. It’s a much needed resource for the freelancing community.

Now go forth and do great things!