Freelance, ho!

As luck would have it, I’d scored my first freelance gig by doing nothing and then having a five minute conversation. But here’s the twist: this industry was completely new to me, and the nature of the project and subject matter only had a passing resemblance to anything I’d addressed before.

A couple of weeks ago I did my first freelance gig; it was a neat experience, so I figured why not write a bit about it?

Getting the Gig

This opportunity came about the way many things do in the real world, via a referral from a friend.

This opportunity came about the way many things do in the real world, via a referral from a friend. A former manager of hers had just started as President at a company, and reached out to ask her if she was interested in doing some freelance work, or could recommend someone who might be suitable. She didn’t have the time to take it on, but thought of me; so I’m sitting at home and get an email with the subject line, “Freelance work?”, and a bit of background info.

I replied:

Thanks for reaching out. That sounds interesting, and I think my experience/skills are sufficiently abstract to be transferable.

Is he a good guy? Like, you’d work for him again? If so, then I’d be happy to have a conversation with him if you don’t mind introducing us.

My friend assured me, “He’s the best. I would totally work for him again.” and then put us in touch.

A very short conversation later, and I understood (broadly) what they wanted me to do: draft a position paper that analyzes a thorny business problem and makes a number of recommendations. This paper, and a summary presentation, will be used by the company and its advocates within the industry.

In my brief convo with the company President, I said that one skill I’ve developed quite extensively is the ability to dissect a complex problem, come up with a solution, and tell the overall story – which is essentially what they needed to do.

In a later email, to be used as part of an introduction, I summarized my qualifications as:

“Perhaps the best approach for this engagement is simply to emphasize that much of my career (and my interests in general – my shelves are filled with books on analysis, forecasting, communications, psychology, etc.) revolves around breaking down complex subject matter into something that makes sense and is useful to a non-expert audience; alternatively, it could be characterized as telling a convincing story with some goal in mind. Previously, that manifested in external communications as bridging the gap between our company and our market, in terms of corporate message, solutions to market problems, and conveying extremely specific technology capabilities. In general, I organize things, striving to bring order to chaos and to meaningfully simplify complexity.”

Much of my career revolves around breaking down complex subject matter into something that makes sense and is useful to a non-expert audience; alternatively, it could be characterized as telling a convincing story with some goal in mind. In general, I organize things, striving to bring order to chaos and to meaningfully simplify complexity.

The President asked if I thought I could get the whole thing done in a week? I said I did, and that was that – we were good to go. So, as luck would have it, I’d scored my first freelance gig by doing nothing and then having a five minute conversation.

But here’s the twist: this industry was completely new to me, and the nature of the project and subject matter only had a passing resemblance to anything I’d addressed before. Still, as I said in my email reply above, I figured it was abstractly close enough to a bunch of my experience that it wouldn’t pose an insurmountable problem.

Confidence, meet Uncertainty

Over the weekend preceding my week of work, the President did a couple of things that got the project started right:

• He sent me a bunch of background information: documents, presentations, links, etc.
• He paved the way forward by emailing all the VPs and other folks in the company who were stakeholders or might be contributors, letting them know that I was coming and that the project was of vital importance; many of those folks subsequently sent me additional background information

So I already had lots of data, and work had been done to get things off to a solid start.

Amusingly, my LinkedIn profile views spiked, and I just pictured all these folks wondering why a tech marketer was being brought in to write this paper; reading my résumé, which is geared towards organizational leadership and technology marketing, there’s very little to indicate my qualifications for this project.

Throughout the weekend, I experienced two seemingly contrary emotions:

• Confidence born of my very strong track record of taking on complex problems and delivering at or above expectations
• Apprehension at the knowledge that much about this situation is new and uncertain: new industry, new company, uncertain corporate dynamics, etc.

I imagined telling my life story many years from now and looking back upon and laughing at my disastrous first consulting experience.

But I thought: worst case, I recognize early on that this project isn’t a good fit, and I let them know as soon as I come to that determination.

To be honest, the main reason I didn’t want to screw it up was because a friend had recommended me, and I didn’t want to besmirch her.

To be honest, the main reason I didn’t want to screw it up was because a friend had recommended me, and I didn’t want to besmirch her.

Having recently completed Superforecasting, I was also reminded of a quote from that book: “Intellectual humility compels the careful reflection necessary for good judgment; confidence in one’s abilities inspires determined action.”

Plus, resigning from my job without having anything lined up is a very clear bet on myself – this project would be a good test and valuable experience, no matter the outcome.

As it happens, I’d also recently completed The HEAD Game, and intended to apply some of its lessons as I analyzed this business challenge.

On Sunday night I drove to Toronto, navigating through a blizzard and listening to the Super Bowl on the radio, with my thoughts a mixture of confidence, excitement, apprehension, and “holy crap it’s really snowy and this drive is taking a long time”. Three freakin’ hours later I’d arrived.

“Intellectual humility compels the careful reflection necessary for good judgment; confidence in one’s abilities inspires determined action.” – Superforecasting

Getting Started

On Monday, I got up fairly early and did two quick bits of preparation:

• I made a resource map: I quickly reviewed the ~20ish documents that had been sent my way; for each, I jotted down the filename, quickly summarized what was in, and made a note of whether or not I thought it was an important piece of the puzzle
• I made a little contacts sheet with all the names and roles of people who’d been copied on the emails to me, with whatever info I could scrounge from LinkedIn

I’m a bit old-school, in that ordinarily I would’ve printed everything off and relied on sticky notes and such, but since I didn’t really have access to a printer, this quick reference resource guide would be pretty useful.

Upon arriving at the office, I signed the usual paperwork and was shown to an empty office.

Urgency vs Patience

I had a very loose plan of attack, and I didn’t know if any formal meetings/discussions were going to be set up.

My plan was, basically:

1. Spend a bunch of time to really get a handle on the business problem; make sure I genuinely understand it
2. Gradually build out the narrative for the position paper, identifying key points and the data that supports them
3. Get a draft done as quickly as possible, to see if I was on the right track
4. Refine and polish as needed, until done

I anticipated that this project would have abstract similarities to my experiences working through two acquisitions my previous company made. In both of those situations, I’d basically parachuted into a foreign office with an incredibly aggressive timeline during which I had to turn around a large amount of technically detailed marketing material.

To pull off a project like that requires the ability to gather and synthesize a huge amount of information very quickly (being mindful of the short timelines), but not so quickly that you make mistakes and end up sacrificing efficiency.

To pull off a project like that requires the ability to gather and synthesize a huge amount of information very quickly (being mindful of the short timelines), but not so quickly that you make mistakes and end up sacrificing efficiency.

This project – abstractly – was the same. I had to understand and dissect a business problem in a new company in a new industry, while spotting signal and ignoring noise, and I had to do so fast enough to get a comprehensive and accurate position paper written in just a few days.

I employed a few of the tactics from The HEAD Game, jotting down factors which I thought were key drivers and determining which pieces of information supported which points.

Really, for most of Monday morning, this was all I did: read the information in depth, jot down some ideas, try to understand a bunch of government legislation, etc.

The President had told me not to be shy about setting up conversations with people, but honestly I didn’t know what I’d talk about – I didn’t want to waste anyone’s time, and I didn’t yet have enough of an understanding to inform any questions. In other words, I hadn’t yet moved from unknown unknowns to known unknowns.

A Breakthrough!

By the afternoon, a few things were falling into place…but I still thought I was missing a bit of the big picture.

But then, luck would strike.

I’d been reviewing some spreadsheets and found some numbers that didn’t make sense to me: for a few, I needed an explanation of what they meant, and for a couple of others I thought there might mistakes.

A member of the finance team had come by to introduce herself earlier, so I reached out to her with my questions. Over about twenty minutes, she explained the meaning of the numbers and took actions to dig into the ones that didn’t seem right.

And then she did something that really made everything fall into place:

“Lee, this is all important background and supporting information, and it’s important to understand it, but I don’t think it really captures the main point, which is X.”

BINGO!

The short conversation that followed unlocked the whole thing. There’d been this major concept which was so well-known to the group that no one had specifically articulated it to me, and it wasn’t explicitly captured in anything that had been sent across. Without this conversation, I could’ve stumbled and fumbled and done my best, and still missed the mark. Instead, things crystallized in my mind and the entire narrative fell into place. All the understanding I’d built to that point served as supporting material for this main concept, X.

I could now give into the urge to start writing, confident that I was on the right track. From about 3pm to 6pm, I banged out a bunch of the paper.

The next morning, I was the first one in the office (I had a blippy pass) and from about 7:30am to noon completed my first draft.

The folks who needed to review it couldn’t do so until that evening, so I drove home.

Rev 2

On Wednesday, I was mainly just awaiting feedback and making little tweaks here and there: filling in some blanks, extending some parts, etc.

I’m confident, sure, but I also knew there was a real possibility that I could’ve missed the mark significantly.

The most important question – whether or not I was on the right track – was answered quickly and positively, so that was welcome news. I’m confident, sure, but I also knew there was a real possibility that I could’ve missed the mark significantly; if that had been the case, I only had a few days to redo things. Instead, as it happened, I had a few days to refine and polish the document…a much more comfortable position.

On Thursday, I returned to the office and split my time between revising and having some in-depth conversations to extend my understanding of particular points and nuances, which of course was then reflected in further revisions.

Around 6pm I sent off my second revision.

Finalizing

A few tweaks came in over Friday, as people reviewed in more detail, and I incorporated those changes over the weekend. I also started on the design elements, as previously I’d only focused on the content. I’m not a designer, so I sent a friend the company logo and colour palette, and he came back to me with a really kick-ass template into which I moved my final copy.

Over the weekend I made a few tweaks here and there, but nothing too major. This document was meant to be clear and succinct, so mainly I looked for ways to optimize content.

Finally, I made a short PowerPoint presentation that summarized the document’s recommendations and supporting points, and on Monday morning I fired them both off the company President.

With his acceptance of and satisfaction with those deliverables, my first freelance gig officially came to a close, and it really couldn’t have gone any better.

Thanks to my friend for providing me with the opportunity, and to my client for setting the project up for success!

Summary of Important Points

OK, that was a fairly long narrative, so it might be worth reiterating some important points:

• Expectations were clear to both parties: one position paper, one summary presentation, one week.
• While I didn’t have direct experience with that company, or even with that industry, I was confident that my transferable abstract skills applied. Folks won’t always see this, of course, but we should at least learn to see it ourselves.
• I have self-confidence and a strong track record, but I also know there’s lots I don’t know; I know my own limitations and am eager to learn. This intellectual humility was key as I approached a new problem and had a tight timeline.
• I applied new skills learned from my ongoing reading. Self-improvement! Arsenal of tools! Always be learning!
• The company President paved the way to success: he secured stakeholder buy-in, and I was provided with a great deal of information even before I arrived at the office.
• I managed to balance my urge to get something done quickly with the reality that I couldn’t really get started until I sufficiently understood the business problem; as it happened, things worked out really well. It was vitally important to get a draft sent out early, to find out if I was on the right track and allow time for correction, but even more important that the draft be good.
• And, most important of all: as far as I know, I did not ruin my friend’s reputation!