Notes for young strategists

This is one of a series of posts that answer questions that I get a lot. I hope this is useful to you.

When I think about the first phase of my career from age 24 - when I got my first copywriting job to becoming a strategist first in NYC then London then NYC - to age 31 (where I lived out of a truck for awhile), there are a few words that come to mind: expansive, thrilling, tumultuous, clumsy, scary. I look back at this first era with affection - affection for what it was for me and affection for those who are in it now. 

I love talking to people in this phase of their life - here are some of the questions that I commonly get and my answers…

How do I become a strategist? 
People don’t judge you for your first job - you start to create your path with how you choose your second and third jobs. So don’t obsess about the perfect first job; just get your foot in the door.

There are all kinds of strategy jobs: social, brand, media, comms… that all need junior roles. Search broadly. Also, lots of very senior talent is going freelance/consulting these days. Reach out to individuals and offer up your services doing freelance junior work. 

Note: I buy into the theory that the CMO’s of tomorrow are the community managers of today. If you love social and can think/create for it, that’s a good place to start. 

What should I be working on?
Learning.

There are a lot of frameworks out there that can jump start your learning. The queen of brand and creative strategy frameworks is Baiba Matisone. Follow her. She’s generous and you’ll learn a lot. There’s also getting to know the industry, the trends, the players, the best practices - Zoe Scaman is an excellent follow. Ed Cotton regularly posts provocative advertising/marketing/ brand prompts that get many people debating (in a good way) in his comments section. Rob Campbell has good hot takes. If you qualify, try to get into the Ladies Who Strategize community that’s run by Kim Mackenzie - it’s a community of people who love creative, social and brand strategy. If you qualify, go for MAIP. 

With these foundations in place, getting good at strategy is getting good at thinking - knowing when to be analytical, when to be creative, what to pay attention to and knowing what is unnecessary fuzz in the data. It's being able to take a shit ton of inputs and boil them down into stories of action. 

Expose yourself to other thinkers. 
Study how they think. 
Figure out how you think. 

Katie Dreke and Stacy Tarver Patterson are exceptional brand + cultural thinkers that are also generous with their brains. He doesn’t post a ton, but I love David Terry’s brain. 

I spend most of my learning time with thinkers and creators beyond the world of brand. Here are a few books that have awakened something in me these past few years - being a strategist means embracing a continuous practice of intellectual, creative, emotional collisions. Books help. Art helps. A local newspaper helps. 

• They Can’t Kill Us Until They Kill Us by Hanif Abdurraqib 

• What If This Were Enough? by Heather Havrilesky 

• Emergent Strategy by adrienne maree brown

• Ways of Being: Animals, Plants, Machines: The Search for a Planetary Intelligence by James Bridle

How do I kill it in my early career? 
No one expects you to know what you’re doing in your first job. Instead, show up hungry and ready to learn. Hunger goes a long way. 

Here’s a quick shortcut to killing it in your early career: your bosses are probably older than you and not as tapped into what’s cool or emerging. They’re spending a lot of their time in management meetings and navigating the politics of your org and the client’s. Arguably the greatest value you can add as a young strategist is staying tuned to what’s going on in the world and packaging that up in a way that your bosses can use it. 

Because ultimately, you’ll succeed when you embrace the fact that your job is to make your boss’ job easier and to make them look good. There’s a few more ways you can do that: 

• Always take notes so you don’t have to be told something more than once. 

• Mistakes are fine. Own them. Talk about them. Learn from them. Do everything you can to not repeat them. 

• Try. Think about how something you’ve done in the past can apply to the ask in front of you and try it. Ask for an example of a similar deliverable and try to apply your work.

• Is the answer to your question Google-able? Then Google it. Don’t ask your boss questions like how to do something in Excel or when the date of a holiday is. 

• Anticipate. Think about what your boss is walking into and what they need. Think about the calendar and ask your boss a question like: I know you have a meeting with your boss in a week - how can I help you prepare for that? 

• Track what you’ve accomplished, learned and stumbled on and ask for quarterly meetings to go over that with your boss. 

Okay I’m moving to my next job - what should I be looking for? 
Ideally, look for a great teacher - in your early days in finding your own voice, teachers make a huge difference. Pro tip: your teacher probably isn’t your Head of Planning or Chief Strategy Officer - it’s your direct boss. I’ve too often seen young people in their career get woo’ed into a department because the CSO is amazing, only to spend maybe an hour a month with that CSO. When interviewing, interrogate the team you’re going to be working with day in and day out. 

A teacher isn’t always a person - sometimes it’s the challenge of the business or the client. It’s totally valid, for example, to move from a small client to being support on a big one as a learning move. Or from a huge agency to a small shop. These are teachers too. 

How do I know I’m doing it right?
I don’t know if this question ever goes away, but I’ve found it has a particular buzzing tension for people in their early careers. I have sat across from countless tense, stressed 22 year-olds who are death gripping a multi-decade life plan that they are trying to design to every last detail, terrified that one wrong move means the whole thing is going to go to shit. 

It is going to go to shit. And be beautiful. At the same time. 

Maybe I’m glorifying my own experience a bit too much, but there’s a big part of me that truly believes that if your 20s aren’t messy, you’re probably not doing them right. You’re going to have massive fuck-ups. You’re going to have equally massive triumphs. And as cliche as it may sound, your job now is to learn. You are the professional equivalent of a stumbling, drooling toddler, grabbing wondrous baubles while learning that bonking your head on the edge of a table hurts like hell. 

You’ll search for the right path. But you don’t ever really know if it’s right because there isn’t one path. It’s just the path that you choose at that moment. 

So instead focus on two things: 

What can I get excited about for two years?
I do my career in two year increments. My brain is too restless and the world is too accelerated for me to meaningfully plan out much further than that. But if I commit to something, I need to know that I can get into it for two years. With a few exceptions, I’ve gotten to the two year mark and have often stretched into more. Overall, I’ve found it much more interesting and realistic to think in smaller increments. Let the pathways open to you. 

Navigation
I deeply believe that the #1 skill we all have to develop in this mad world is the ability to tap into our own self to navigate towards what’s next. Yup, I’m talking about the woo part - the tapping into your truth, the connecting with your power, knowing what motivates you, sitting in silence and letting the universe in… all that. The traditional paths are dead - we have to create our own meaning and pathways. Whether it’s meditation or journaling or finding that activity outside of work that gets you in a place of flow and connection with what you’re about, cultivate it. 

If you could do it all over again, would you do the same thing? 
Maybe?

What I do like about what I did was: 

• I spent my 20’s in hardcore learning mode AND it was exciting and fun and I met amazing people

• I expanded beyond advertising in my 30’s a worked in different spaces

• I founded things. That’s critical in being a real advisor to others who are founding and running things

• I’ve moved into a senior advisor role in my 40’s - going in deep with leaders and helping them navigate key challenges

• I’ve always embraced risk and challenges and pushed how far I can take my core skillset and that’s taken me to unusual and exhilarating places

Whereas I think that storytelling and narrative change is very interesting, I don’t feel the same way about advertising and marketing. Because here’s the truth: advertising is the thing that gets added on at the end; the real decisions are further upstream. And I don’t think the world needs more marketing and advertising as we know it; we need more organizers and power-hackers and innovators and activists and builders that have the stories they need to clarify their work and get shit done. 

The bulk of the work I do now is to help others develop strategy and stories that drive action. It’s not the work of advertising; rather it's the work of strategy + storytelling. The world doesn’t move without stories and adding that upstream value is a gratifying place to be. 

I think I’ve always been a storyteller, so perhaps this was the right path. But sometimes I think if I could do it again, I might have started a space where stories are more closely applied to social change - perhaps politics or activism or organizing or policy or law - and not detoured through advertising. 

Who knows? It happened the way it was supposed to. 
And your path will as well.