12 months ago I took a leap and decided to freelance. One year later, these are some of the things I talk about when people ask me what it’s like.

#1 Managing your own hours is a superpower.

The ability to choose your hours, in terms of when and how many, does incredible things to your happiness. Early on I decided to work no more than four days a week in big agencies. This created time to work on other projects (paid and unpaid), chase new ones or just enjoy a sleep in on a Friday.

The changing cadence also keeps you interested and interesting. I did everything from a three month contract to one project which was literally half an hour. You can choose to focus on one big thing, or juggle ten smaller ones. The latter meant I could do a 15km run in March, which was only possible because I dropped everything at 11am and went for a jog when I wanted to.

You do need to be buttoned down on your calendar management. Even then sometimes things don’t always line up. I’ve accepted a few days of work, then 10 minutes later had to turn down a bigger gig because you’re already committed. Sometimes work just disappears too – I was three days into a month-long pitch which got pushed out by months. Annoying when you’ve already turned down two other jobs to be there.

But that’s freelancing life. The contracts always favour the employer (but you only get them from bigger agencies). It’s why they pay you more.

Despite being the master of my own calendar, my grand plans to work on side projects failed miserably. It’s rather easy to take on more paid work or spend time meeting people for coffee while passion projects collect dust.

#2 Choosing who you work with and what you work on, helps navigate your career.

Freelancing allows you to pick the types of brands, agencies and people you work with. And the projects you want to invest time in.

This year I worked with big agencies, small agencies, entrepreneurs, starts up and consulting my own clients. But you also have flexibility in the role you play in the work you say yes to.

You can reinvent your job title (and yourself) with every new project, pushing into uncomfortable spaces to play around with. One of my favourite adventures this year was developing the marketing strategy to launch a gluten-free brewery. Not quite my heartland of creative strategy, but a category close to my stomach, and a rewarding project which has become ongoing. Throughout the year I picked up everything from writing content strategies through to delivering full service campaigns white labelling freelance creatives under Pigs Don’t Fly.

You get to flirt around and try on different hats. One year later I have a much closer idea of where the intersection is between what I like doing, what I’m good at, and where the money is.

#3 The market for freelance strategists is good right now.

I am fortunate. I have a good-sized network built from nearly a decade in two large agencies. This created most of my opportunities.

I also have somewhat of an audience (you suckers) – writing here and on places like Mumbrella helps keep me top of mind as a potential resource. In two cases it also opened new doors which turned into work.

I also realise I fell into an attractive role. I’d suggest large parts of my success aren’t because of how good I am, but rather a lack of freelancer planners in Melbourne. If I was a designer, I’m not sure if I’d be writing such a romantic post.

I also managed the whole year without using a recruiter. They eat a decent piece of your day rate.

Without being arrogant, honestly my biggest challenge was learning to say no to work. Especially early when I wasn’t sure what my income would average out to. Even still it’s bloody challenging turning people down – knowing the opportunity cost and wondering if you can find time after hours to make it happen. Even to this day I wonder if I got lucky and am still in a honeymoon period, and should be making more hay while it shines.

With the ebbs and flows you do sometimes find everything crashes at once. I’m doing more weekend work now than in my permanent life (which my former colleagues will tell you wasn’t much). Other times it’s quieter than you want it to be. I got some advice to make the most of those days – get out of Melbourne and spend time at your beach house. If only I had a beach house.

#4 The money is great, but you have to learn how to earn it.

The money is really good. I finished the year 36% up on my old salary.

But it takes time to learn what you’re worth. And even longer to be confident enough to ask for it. I sold myself short for at least my first two gigs. To this day still need to stop negotiating myself down unnecessarily, often before the other person has even responded. Never has your imposter syndrome screamed louder than when someone looks you in the eye and asks your day rate. At least these conversations happen frequently, so you get good at it fast. You learn to throw your number out there and then stop talking.

Eventually I worked out to be stupid and arrogant enough to ask for what I thought was a stupidly high day rate. And they said yes. And keep saying yes. I do wonder how this dance impacts men versus women.

If you’re thinking of freelancing, my advice is to add at least 25% on top of what you think you can get. Push as far as you are comfortable and then a little more. Remember you are covering down time, your own expenses, equipment, annual leave, sick leave, training, work beers, etc.

I unsuccessfully gambled with remuneration. Twice on pitches I cut my rate in half, adding 50% on top if we won. Neither paid off (although I did help win other pitches!). I also did one job for cryptocurrency – right now it’s down 60%. This year I’ll stick to cash.

Along with good calendar skills, you also need to run a tight ship with your bookkeeping. I manage mine through an unnecessarily detailed Google Sheet, which works for me. I also manage my own quarterly tax statements (it’s easier than you think). Paying your own superannuation and tax annually does take discipline – eventually I created a separate account and moved the money out of sight.

The cliché of chasing invoices actually wasn’t too bad. The big agencies sometimes drag their feet, but 90% of my invoices would have been paid within three weeks.

#5 All big agencies are the same, but some have better culture.

Most agencies look and smell the same. The people who work there are kinda the same too. They tend to dislike their clients, work longer-than-healthy hours and think the chaos is unique to their agency. But they are good people who come to work every day wanting to do good work.

Culture is distinctive though. You notice it particularly as a freelancer where you see lots of it fast. It’s most evident in how much an agency encourages you to get among it or put your head down and work. It’s a bit like gravity – you can feel it immediately but it’s harder to see the cause. Sometimes you can tell in the first ten minutes, particularly when someone in IT tells you they don’t allow freelancers on the WiFi.

I didn’t realise it until this year, but in my permanent life I was spoiled with access to coffee machines. Seriously agencies, sort this out!

#6 It’s not all fun and games.

Not having a work crew sucks. I miss the daily banter. Having worked in bigger planning teams in the past, it’s also tough not having another strategist to throw something around with.

Working from home for too many days in a row isn’t heathy either. Especially in winter. For my next stint at home I’m going to find a temporary coworking space.

Unfortunately you rarely get to see work through. You come in, do your piece, and you’re out. You don’t often get the opportunity to nurture and help ideas grow. Last week I saw an ad for a strategy I wrote six months ago which I thought got killed. It wasn’t a very good ad.

It’s also challenging not working toward something bigger. Freelancing is constantly short term. You need to be comfortable with not knowing what’s happening next week, and not relying on fulfilment from big career-defining moments which take time to build up to.

You’ll be tempted into permanent work. I had a few full time and part time offers, one including equity. But while it’s not all sunshine, there’s still plenty to love because…

#7 Freelancing is awesome.

You meet heaps of people. You learn a lot, fast. You rapidly get the opportunity to steal elements you like and learn to avoid those you don’t.

Critically, you get a license to be brutal with recommendations. There’s no client baggage or incentives to get involved in politics. It sounds counterintuitive for a strategist to say, but not being committed long term allows you to approach work with an attitude of “My contract finishes tomorrow, so I don’t care what you decide – but this is the right recommendation”.

My work this year has been better because I was more empowered to take a step back and challenge the client, rather than just answering them.

And finally, I worked out that agencies only bring in freelancers when they need help. So if you can be even a little bit helpful, everyone is bloody happy.

– – –

If you’re thinking about freelancing in advertising, shoot me your questions. I’d love to share my invoice templates, advice on day rates or tell you which agencies have craft beer in their fridges.

Last year I missed a connection at Heathrow Airport. I sourced the needed documentation, filled in the forms and submitted my $201 travel insurance claim. Four weeks later I got a cheque in the mail for $1. When I enquired why it was so little, they told me there was a $200 excess. I suggested some feedback:

Me: You should consider putting a reminder at the start of the process. It would have saved us both a bit of time.
Them: It’s in the fine print of the Product Discloser Statement.
Me: Yeah… I get it… but… never mind.

Good feedback ignored. Which has become the standard, particularly on social media where the general sentiment is “Thanks, we will totally pass that onto someone who matters and definitely not ignore it.”

Instead of stopping a moment to listen, businesses are too busy screaming for feedback. Last month Amex sent me three reminders to fill in a survey. Expedia asked for a review when I checked in, when I checked out and then a follow up.

You pretty much can’t interact with a business now without being prompted for a survey.

Marketers are too obsessed with their Net Promoter Score. They’re not seeking feedback for improvement, they’re trying to hit a KPI.

But unsolicited feedback is where the good stuff happens.

One of my most successful strategies used old Facebook comments from customers enquiring about a discontinued product. The client had previously dismissed them with a generic apology. Instead we used them to build a business case to bring the product back for a limited edition run. It was so successful it became a regular, and went on to do more than $4m in sales.

Too many business ignore genuine feedback because they’re soliciting feedback that’s shit. Imagine a business culture where the brand listened, recognised, implemented and then thanked. Even rewarded.

Instead, we just get fucking surveys. And useless chatbots.

Nearly 12 months ago I quit my job and started freelancing. With the opportunity for a fresh chapter, I stopped calling myself a Digital Strategist and updated LinkedIn to Creative Strategist. Here’s why.

1. Digital Strategy has changed.
When I started my career, “digital” was a blurry word. It was a grey area you could carve your own definition into. I’ve been lucky for most of my career, in agencies where I largely got to shape the kind of work I wanted to do – finding opportunities for ideas on digital channels. But increasingly, Digital Strategy has nothing to do with ideas. It’s more “transformation” and “enterprise solutions”.

These days the role requires a strong understanding of specific technology tools and data platforms. You have a seat at the table, but it’s not necessarily with marketers. The consultants would say that’s a good thing. And more profitable. But I like writing briefs and working with Creatives.

Unless you love CRM or DMPs, there’s no longer room in agencies for Digital Advertising-ish Strategists. (And rightly so, see below.)

2. Digital is just a tool.
Why do we have Digital departments in agencies? Or Digital Creative Directors? Digital Strategists belong on the same list of obsolesce.

Digital is just a channel. Usually for hosting an experience or distributing a message. But it’s not always the best place to host an experience or distribute a message. Yet if you have Digital in your title, you have a natural bias. Not making that recommendation makes you less relevant.

But Strategists are problem solvers, and they can’t have predispositions to certain tools. To a hammer, everything looks like a banner ad.

3. “Digital” makes me feel a bit sticky.
There’s too many snake oil salesmen out there. And yes they’re mostly men. With oil comes their greasiness. Too many entrepreneurs selling courses for Facebook ads. Too many videos of Gary Vaynerchuk telling you to hustle. Too many digital marketing influencers without any influence (or something to say).  Of course, I generalise. There’s plenty of legit digital thinking legends out there – it just feels like they’re getting harder to find.

4. You can charge more.
There’s more demand for Creative Strategists, and fewer in supply. A Planner who “gets” digital seems to be the sweet spot, more so than a Digital Planner who considers brand or a proposition. People don’t like talking about money, but from what I’ve gleamed, day rates are better for the agnostic problem solvers.

5. I’m finally starting to understand how advertising works.
I’ve worked in advertising for nearly decade, and am only now just starting to feel like I get how it works. And every time I read more, the way brands use digital pulls in the direction opposite of effectiveness. My (ever forming) philosophy is guided by the likes of Byron Sharp, whose work suggests brands grow through mass reach of potential buyers by building and reinforcing memory structures to increase mental availability. Even if there’s too many buzzwords in that sentence for my liking – that’s not  how most brands invest in digital.

Likewise I lean toward the notion advertising works because it is a signal. It’s an investment received socially. Traditional ads work because they are perceived to be expensive, collective and seen in unison. Digital is the opposite: cheap, individualised and sporadic. As Rory Sutherland says, “We make our wedding vows in front of a large number of people simultaneously.” Presumably at an expensive wedding.

Generalising again, but it would seem most of the people flogging digital thinking don’t have a philosophy on how advertising works, or even believes that it does.

I don’t think we can attribute this one to David, but Ogilvy sum it up best: Digital is dead. And so, I ditched the word from my title.

Although you’ll still find plenty of mentions in my bio for SEO. You can’t take digital out of the boy!

If you think for a living, you should write more.

For obvious reasons, like to share your wisdom. And build your street cred.

Even if you don’t have wisdom or hate the phrase ‘personal brand’, you should spend more time writing things down. Capturing thinking, yours or someone else’s, publicly or private, forces you to process it. For me it also takes it out of my head to make room for something else.

Thoughts, ideas, frameworks, tools, quotes, presentation material – anything worth remembering. Or stealing.

Last year I started freelancing and got organised. Here’s how I capture thinking by writing it down:

Moleskin Notebook
In the past I’d capture all notes in a Moleskin. To Do lists, client data, doodles. But these are almost always disposable. Now I write everything on a white A4 piece of paper, folded in half. At the end of each week I throw it away.

The good stuff, I transfer into a single notebook, the front page you can see above. Doug Kleeman calls it writing your own textbook. It’s for the timeless stuff – lessons on how advertising works or how to be a better problem solver. Things you might refer to in five years.

Strategy Library
I have a folder on my MacBook that houses every good report, framework, paper or case study I read. It includes pieces of work from other people/agencies, even well designed decks for inspiration. All of which is carefully filed, building up over nearly a decade in advertising.

Strategy Cellar
It’s an online version of the Library, kind of like my personalised version of Julian Cole’s Planning Dirty Cheatsheet. It’s a toolkit, with resources and tools I refer to. A Google Sheet works nicely.

This Blog
Of course, there’s this blog. Even if no one reads it, it’s where I can distill and build on thoughts. And identify themes in my own thinking. I can’t tell you how many times I’ve done presentations only to later realise they’re repackaged blog posts. You might argue Twitter plays this role for micro thoughts too.


Where do you write things down?

Okay, not that old fashioned.

I’m sometimes criticised for stirring the pot without providing an answer. Like my last tirade against brand immaturity on social media. If you didn’t disagree with that post but were wondering what to do – here’s how I’ve been strategically thinking about brands on social.

I have a love/hate relationship with Facebook. I think their customer service sucks, they lie to brands, they pulled a rug from under us and Mark Zuckerburg is Lex Luthor. But Facebook isn’t going anywhere. Despite its flaws, its cannot be dismissed.

Most brands know this, and have jumped in head first. But they suck.

Since I started freelancing the most common conversation I have with clients is telling them they’re social media strategy is bad. They’re wasting time, effort and money. Often because of an approach sold to them by parties with vested interests or a limited understanding of how advertising works.

Here are some red flags you might raise with your current agency/snake-oil-social-media-expert:

  • You measure success (or worse, invest) based on page growth/likes/followers
  • You measure success on engagement
  • Your strategy is built on ‘organic reach’
  • Content is promoted indiscriminately
  • You spend more on content creation than content distribution
  • You’re creating more than one piece of content a week
  • Your content consists of stock imagery or is sourced
  • You don’t know what a Relevance Score is

Facebook, Instagram, Twitter, Snapchat – they are all media channels. And we must treat them as such.

This means a return to good old fashion advertising. But using the new opportunities these modern channels bring.

The notion of building communities or interaction is a myth. And largely it exists on unproven hypotheses, and a good dollar margin on content production. Content creation can be very profitable, and therefore is an attractive recommendation for vendors. What they won’t tell you is to be most effective you should be investing 80% of your budget into media. Because here the margins are a minimal (and continue in their race to the bottom). It’s also a skillset that doesn’t sit with a traditional creative agency.

The truth is, there is no content beast that needs feeding. The most important word in social media is not “social” but “media”. Do not invest in high volumes of content, instead focus on reaching potential buyers.

Of course, making good content is still important. Facebook rewards brands that do (if you haven’t already, research Relevance Score and its role in increasing your reach).

Brands should be doing fewer things better. Create only a few killer content pieces and nothing more. You know where the rest of the budget should go. I’m going to take a guess and say you’re not at risk of over saturating your audience. If you’re feeling bold, make one great piece a content a quarter – setup the media to reach many with a low frequency.

There’s no need to post daily, or even weekly. This means content calendars are largely redundant.

Instead think about programs. One of the key technology benefits in digital is the ability to target people through a marketing funnel towards conversion. Use your marketing plan to build relevant messages for each audience at each stage. Definitely do not worry about International Talk Like A Pirate Day.

Another benefit of digital is our ability to measure. Forget about vanity metrics, instead build actually useful plans to measure brand and ad metric uplifts based on exposed versus unexposed audiences. Or use third party shopping data to understand actual buying behaviour.

This is how brands should be building social media strategies in 2018.

In many ways, it’s a return to the basics. Create ads that build saliency and distinctiveness. Then spending money distributing them to refresh memory structures.

Without intending to, I wrote a three-parter on the current state of uselessness of brands on social media. I took umbrage at:

These are lazy strategies. They are easily copy and pasted (and often are), lack insight and usually lead to work that is generic and uninspired.

Unfortunately, they often work. At least in the short term, in so much as bullshit metrics like Engagement Rate. If you do the above, it will get you a handful more likes. Even a lift in ad recall. But this is not how you win. (In same cases it may even do harm.)

This is what happens when you give the kids a seat at the grown up’s table. (I know, I’m one of them.)

In the past it didn’t matter because social and content had little impact. You’d joke saying it was a good job for the intern. But now, rightly or wrongly, brands are investing more time, effort and spend. Suddenly this activity is being seen and heard, with scale.

Yet it’s still the same unexperienced marketers behind the wheel. They’re just not driving go karts anymore.

Michale Goldstein compares it to fishing with a line or fishing with a net. To bastardise his analogy, line fishing has an immediate return but it’s one fish at a time. Net fishing is a long game, with no quick wins or visible short term result. But they haul more fish eventually. And have the infrastructure to keep hauling every year.

Brands on social have forgotten how to fish with their net.

Peter Field has proven brand building drives long term growth. And everyone’s favourite marketing academic Byron Sharp says “Most of your sales this year come from work that was done in the previous twenty.”

Do we honestly believe the Bachelor reference you tweeted last week is going to impact your customers’ buying behaviour in 2037?

We need the grown ups back. The ones who have been around long enough to understand how to build brands and think long term.

Today Pigs Don’t Fly turns 10.

From the very beginning it was naive and too often arrogant. But my early writing is a good reminder to voice a opinion, especially when it’s controversial. And don’t do too much self censoring – it’s okay to piss people off occasionally (especially when you’re right).

I certainly write far less than I used to. In 2008 I wrote 153 posts (most of which were rubbish). In the last twelve months I published 15 (still mostly rubbish).

What started as a side project at university quickly sparked an interest in writing. It became somewhere to explore digital marketing, and later brand, communications and entrepreneurship.

It got me a foot in the door to advertising and helped build my personal brand, for want of a better term.

In many ways it’s come full circle, back to being a side project. In 2009 I did 45k pageviews, this year I’d be lucky to reach 10k. The once-thriving Australian marketing blog scene is largely dead.

If I was smart I’d probably be publishing on LinkedIn or Medium. And I’d definitely have migrated from Blogger to WordPress (which has been on the To Do list for about eight years).

Most recently, Pigs Don’t Fly has become the banner under which I freelance. We (read “I”) just had our first project signed off that requires people other than me. I guess it’s an agency now?

Above all, it remains a place to think out loud, collect my thoughts and occasionally write something people read.

Thanks for being one of them.

Animated Gif Product Shot

Product shots have became a default strategy on social media. Especially for brands in FMCG, alcohol and retail.

And it’s a sign we’ve hit rock bottom. We’ve regressed into the lowest cost, lowest common denominator approach to social.

We’ve forgotten comms need a strategy and an idea. And how to think long term.

Somewhere, somehow, we convinced ourselves flatlays would create meaningful business impact.

I mean, you wouldn’t even use a product shot in old school media without a price point. But I guess if you animate it as a boomerang that makes it better.

Not to say there’s not a role for them. Product shots might be the reinforcement a person needs to convert further down the funnel in your content marketing engine. But you’re not going to change behaviour with just a well-lit cinemagraph.

Even worse is the approach of reposting user-generated content. Usually as a product in some punter’s hand. No concept. No strategy. Not even some art direction. If you think anyone’s being persuaded by this except marketers you’re delusional.

(Nothing against driving UGC. It leverages the real power of social – the network. It creates social norming and reach with advocacy. But that doesn’t mean brands create value in broadcasting it.)

And it’s not just social publishing either. We pay “influencers” to take photos of our products. Even better if they’re holding it!

(Note the deliberate use of quotation marks. Read any number of articles on bots which generate fake interactions or the concept of an ‘engagement pod’.)

Or the epitome of modern advertising, paying six figures for your product to replace someone’s head as a Snapchat lens. But if you open your mouth it animates so I guess there’s that.

It’s usually the Strategist who wants to shoot the Creative or visa versa. But we’ve watered down social so heavily they probably both want to put guns to their head.

How did we get here?

Definitely a lack of experienced marketers and advertising folk making decisions. More on this in another post/rant.

We’re also lazy. You don’t need an insight or a concept for a product shot. And the margin’s healthier because of it. It’s easy to get your hands on product and shoot something with decent production quality. Especially when most agencies look like converted warehouses.

Fortunately within every problem is an opportunity. The very last brief I wrote before leaving my previous agency turned into a series of product porn piss-takes:

Easy Roller Social Content

Don’t forget kids, product shots don’t build brands. And you’re not going to win the battle for attention without an idea.

Once you’ve developed a creative strategy, written a brief, got a concept and sold it in… there’s still plenty to be done. The next stage is a comms strategy – finding the best way to spread your idea to the right people through the right channels. More often than not, you do this with media.

And it’s rare these days to see a media plan which doesn’t include Facebook. Facebook’s revenue grew 62% in the US last year. Between them and Google, they receive 85 cents of every $1 in digital growth.

Which is problematic when it doesn’t work.

The above error message is what a client of mine saw the day they went to push a major campaign live. No context, no means to solve and no help anywhere online. Especially not on launch day.

This is a pretty standard level of service. Facebook are notorious for giving little support unless you spend big each month. If you do manage to track someone down, there’s usually nothing they can do except escalate, whatever that means. And conversations with online support yield little, to a point where you wonder if you’re talking to a bot.

In the end there was nothing to be done except for my client to wait it out. Six days later it was fixed. And the only reason they knew was because we were checking daily, not because we were notified.

That’s six days a client wasn’t able to be in market. Six days of opportunity missed and sunk production and resource costs.

With any other media owner, it would be completely unacceptable. You’d remove them from all future media plans. At the very least they’d work with you and your client to make the rectify the problem, or give bonus value. You’d definitely get a response to your emails.

More than ever media owners need to do everything they can to win and keep your media custom. (Although to be fair some of them are hopeless too. Last week I reached out to two sales reps for a client looking to spend $50k with each of them. Neither got back to me.)

The sad part is, despite the huge fuck up, Facebook’s monopoly means they’ll still be on the media plan next time. Probably with a 62% increase in budget.

Unfortunately I’m yet to see a brave media planner tell a client they’ve removed Facebook because it’s not in the industry’s best interest long term. And margins are so thin it’s in the agency’s best interest to avoid fragmentation anyway.

We’ve shifted an awful amount of spend and therefore power to Facebook and Google. And in doing so we’ve painted ourselves into the corner of a seller’s market. Which is very problematic, but no one seems too worried because we’re losing our ability to think long term.

Today is my last day at Cummins&Partners.

I’m closing what has been an excellent chapter in my career. For five years I’ve worked on some outstanding brands and business problems. I got the opportunity to build and manage a content department. And I learnt from some of the best (and funnest) in the business.

As of Monday, I’m a freelance digital thinker. The plan is to dust off a few side projects too and write a bit more.

So if you need a problem solver who understands how brand, creativity and media engage consumers through technology – buy me a beer. I promise I’ll make things much simpler than that last sentence.