I recently interviewed Kevin Chesters (you can watch it here), and boy what a dream conversation it was. Kevin has a wonderful way of being both a very smart man, and a very generous one as well with his thoughts. And although we never worked together, i could see a level of thoughtfulness that frankly i wish more CSOs displayed. Rare stuff.

Anyway, heaven forbid i discourage you from watching the full thing. But at the same time, sometimes we're short on time and headspace to watch YouTube videos, so i left a few notes below as well. It's a proper good conversation, and Kevin even laughs at my jokes (always a sign of great integrity), but here's some of the main things i learned.

Strategy's role

Let's face it, you and i suck at explaining what we do to anyone who doesn't do what we do. What is the point of a strategist? Surely not slides, though it feels sometimes that's all we're reduced to. Kevin had two good articulations of this. We're here to help separate the useful from the interesting. Or, specifically with creatives, we help unstick the stuck. Gonna start throwing these around dinner parties and seeing if they stuck. Chances are, they won't. But as far as understanding our own roles in a memorable way when mentoring young strategists, these two are bangers.

Creative process

Kevin thinks we glorify the proposition. I agree. There's so much weight put onto that one box in our briefs, which usually has a higher typeface size, or it's in bold or italic, to show it's "the one thing" that we should think or do. And look, i get it. But the reality is, my experience has been much more fruitful when we approach the creative process as an informal, conversational approach, where the brief emerges from a discussion, rather than preceding it. And if it's good enough for Kevin (who has worked in this industry almost longer than i've lived), then it's good enough for me.

Work culture

The fact we're both in the consulting space gives us certain privileges, one of them being we can talk about how we're against the glorified overwork culture that defines most agencies (too many). This isn't a dig to individuals, rather a general critique to the way the business model and cultural systems of agencies encourage this. Sell time, you're encouraged to spend a lot of time on things. Sell outputs and deliverables, where it matters more what you deliver rather than how you deliver it (or how long it takes), and the story starts to change.

Time and money

These two concepts change fundamentally once you enter the self-employed game. On the one hand, you lose the sense of structured income, which makes us asset managers (our own, that is) who happen to sell strategy as well. In practical terms, some projects may compensate well enough that they cover the next 3 months. So while ideally we do loads of those to keep cash flow healthy, in reality we're building cash reserves to endure the harshest times of project famine. And this is the game. The other part of the game? Weekends become a strange concept. Sometimes we do work on a Sunday evening and then take Monday off. It's strangely liberating, once you get around it.

Business realities

Running your own business (that is what freelancing is, and the quicker we reframe this, the better for us all) means you, well, get better at understanding business realities. Your own – can i afford to spend time "building my brand" if i'm not getting the short term cash flow i need –, and therefore your clients. I think our industry suffers from a severe lack of empathy for our client's own restrictions at a business level. Companies are human-made systems and therefore there's a fair degree of irrational (though not illogical) decision-making which we love to bash when we look at it from the outside. Point is: once you're in charge of your own bottom line, you respect the decisions that clients do in order to also protect theirs. The difference? No one's hunting for your budget in your own company.

Total transparency

One of the most refreshing business conversations i had recently was around loyalty. "I need to talk to you about something before we start working", a client said. "I really value loyalty, so if this goes ahead and goes well i'd like to get a verbal commitment from you that we'd work together again on other things". This was from an agency CEO, who was afraid other agencies might poach me for jobs. I can't tell you how much i appreciated this level of honesty, and so far the relationship is going, frankly, great. This level of honesty is something i aspire to with clients as well. Running your own business has a funny way of making you more assertive about how you express your needs. Not in a way that is arrogant, but in a way that is clear. State what you need, and go from there. Faffing is not helpful.

Payment challenges

One of the least sexy sides of running your own business: chasing for payments. We didn't discuss this, but reminds me of a great piece of advice i will now leave with you. If you run your own business, even if it's just you, always have an email that isn't yours for admin stuff. You can even call it someone's name (let's say, for argument's sake, it's deborah@salmonlabs.co). The point is very simple. Any tough money conversations, Deborah will handle it. That gives you license to be stricter (when in fact we're just enforcing the rules you originally agreed), without feeling like it's tainting on your reputation as the business owner and lead consultant. Sorry about Debs, that's how she is!

Pricing opportunities

You know the classic "we don't have a set budget, how much would you charge" conundrum? Kevin had a great piece of advice on this. 10 million pounds. That's how much i'd charge. Suddenly, you do have a set budget, and it's definitely not 10 million pounds. Now we can start talking about what's feasible for you, and go from there. One of the most underrated things we can do with clients is propose something not because we want them to accept it, but because we want to gauge where the limits are. It's true for strategic thinking and ideas. Also true for money. Once you know there is a limit, you can work backwards from there. Only got £3k? Cool, here's what we can do for that.

What next?

I'm so glad you asked. If the above sounds like it's a solid set of conclusions from our conversation, then you should go watch the full conversation here. I missed tons of good stuff, and Kevin is such a fountain of knowledge. I just wish more CSOs had this level of openness about how to make strategy feel like a thoughtful and accessible practice that we can all learn to get good at (in my case, less shit), instead of coming at it from an agency-shaped ivory tower. Learn more about Kevin Chesters here.

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Rob Estreitinho Strategist, writer, maker ​ Whenever you're ready, here's 2 ways i can help you: ​Join the Salmon Crew. Access our private WhatsApp group, where you'll find a safe space to help you stop overthinking strategy. You'll get daily memes, questions, quotes and links, help from other smart folks, you can be a guest on future panel events, and get to shape the future of Salmon Theory. Join smart minds from Leo Burnett, Genius Steals, System1, Flight Studio, VML, Miami Ad School, and more. ​Hire Salmon Labs. We're the strategy studio that helps savvy brands swim upstream. From brand, comms and content strategy, to training on creativity and how to use AI, we like to do things in a fast and bespoke way. No fixed methodologies, moments of grand reveal or complicated language. Just pure shared problem solving.

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