Thursday , 25 April 2019
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How to go about making money as a strategist

The best piece of advice I have ever received in my career was:

Greg, you are not going to work here forever, two years would be a good innings, you should not want to work here forever, the way you learn and start making money as a strategist is to move around in the agency world, not staying still too long.

Making money as a strategist

Making money as a strategist

That was given to me by the founder of the first of the design agencies I worked at on my third day within the company, indeed my third day of working agency side (having previously done three years client side in financial services).

As you may expect I was a bit shocked but now, six years later, I am looking back and he could not have been more right.

I stayed there for exactly two years before being made redundant, although in truth I had already decided I was going to leave but had not heard back from an agency in New York, then I freelanced for a year at what I know now was a ridiculously low rate but one that meant I started making money as a strategist in my own right.

From there I took one more leap into the full time arena – although I now refer to it as a ‘long contract’ as I was paid well but ultimately made redundant again when the strategy team got culled back to just the head of strategy.

Since then I have been working for myself, on my terms, across a number of different retail design, service design, packaging design and brand design agencies in five different countries. This is the way you start making money as a strategist.

Interestingly though, with each move I have been able to charge more and change more.

The key to making money as a strategist is to work hard, listen a lot, learn a lot, understand a lot, and add a lot (of value). Sounds obvious, right? Well it is, but the one thing missing from that list is to move on. That’s a piece of new career advice that is often left out.

I do not mean move on just for the sake of it but when it is right for you – be it you know you are not going to get much further in a given place, you realise you were sold a dream at the beginning or even if you have absorbed enough to consider yourself, honestly, to be able to make the step up to the next level in another design agency.

Strategy is not all about money – as much as I love my weekly invoice time (I really do, still novel even now it is mostly automated or done on the move from my phone – thank you Pages app on iPhone and iPad) – the one thing that will make you make more money in the strategic function is… passion.

I love what I do, I live it, breathe it, chat about it and rarely switch off from it… for example, when my fiancé and I go shopping she cannot be with me if we are in a supermarket, she will literally go do the shopping whilst I stare at any given category (whether they are a client or I spot an opportunity for a potential client) and take photos, write ideas on my ever-present Post-Its or simply buy an entire competitive set just to analyse it properly when I’m back home.

That is what stands me out from many.

The cash is great, but that conversation is 5 minutes at the beginning of a project – ‘What’s your day rate?’ – ‘£xxx’ – ‘right, how about £xxx’ – ‘well I could do it for £xxx and we are both kind of happy’ – ‘done’ – ‘right, admin over, what’s the detail of the gig’.

From there I submit the invoice to the relevant office or finance manager and just get on with the job, and become one of the team, wearing their badge and trying to get them new business where possible – why? Because I would then be the most qualified to work on that new business.

What are your experiences of climbing the strategic pole? Do you think there are other ways of doing things and getting on?

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About GregDillon

Greg is the founder of strategy consultancy GD | Inspires and spends his days strategising for various design agencies and clients around the world - see more at He is also a prolific entrepreneur having launched - a website aimed at giving advice and insight to new, existing and veteran freelancers as well as commenting on all things strategic. Feel free to email him at: or follow on Twitter @StratTalking


  1. Bruno Rocha de Almeida

    Hi Greg,

    I’ve landed in the “strategy world” two years ago after experiences in marketing and media planning. Here in Portugal there’s not a Strategist’s culture and the role is not as valued as in anglo-saxonic countries.

    A friend in a branding agency based in London invited me to help them in some projects and I provide them some strategic guidelines but, before that, I have never imagined the existence of freelancing work for strategists…

    So, reading this article made me realize that there are more possibilites to make money as a strategist than to simply join a company. Don’t know if freelancing really works in countries like Portugal, but maybe it’s just a matter of knowing the right people and have the guts to try it!

  2. Hi Bruno,

    It is all a matter of making connections with people and seeing where you can fit in with their workflow to make their lives easier and provide an expert opinion / service where they may not know the intricate nuances of your niche.

    I do not know Portugal that well in terms of freelancing but with the web there is no barriers to who you can do business with, I work for agencies in San Francisco and Singapore for example and have never met the guys – they were put in touch with me by my existing clients referring me.

    Are you currently working full time with an agency? What kind of projects have you been working on?

    Strategists can earn a good living through freelancing – I’m planning a rough guide to day rates soon so look out for that to see how to leverage your know-how.


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