Asking Not Asking #22: Jack of All Trades

Asking Not Asking #22: Jack of All Trades

TINA ESSMAKER / Creative Coach

Dear Tina,

Last year I worked as a supervising art director on the film Midsommar by Ari Aster. It was one of the most gratifying jobs I have ever had. I got into the projekt more or less by chance and have no real prior experience working with feature film, but I am very pleased with the result of my work. I would like to do more like that. Work on longer projects, as a freelance, but be able to cooperate and “dig in” more than I usually do as a graphic designer. And apply my skills and my craft in a context that has art as an outcome.

I have always been very keen on moving around as I have looked at other creatives careers which often seem to end up in a situation where you do the same thing over and over again. The built in problem however is this commodification of yourself as a freelancer, that your next opportunity is more or less based on your last one.

Everyone loves a creative that is multi-skilled, but when it comes to hiring, everyone loves an expert, and why shouldn’t they? They need someone with a solid track record of getting that specific task done. For me this has been a problem my whole working life: drawing the benefits of being a freelancer, being able to choose projects, but at the same time being pushed.

I’m not sure how to make a move into the film industry since it is not my usual line of work, and also I’m geographically way out of the way in Stockholm, Sweden. And I guess the underlying dilemma is that I’m not sure how to maintain the idea of myself as a kind of “jack of all trades” or to make some kind of active choice and promote myself as a product/niche service.

-Jack of All Trades


Dear Jack of All Trades,

Ah, the age old question of whether to be a generalist or specialist. Do you continue to diversify your experience and skills, knowing just enough in each area, which might cause you to be overlooked by employers who want someone with a specialized focus? Or do you specialize and dive deep, foregoing other interests at the risk of losing relevance if your area of expertise is edged out of the industry? All of us ask this question at least once in our careers. It can be challenging to predict what employers will want in the future or what trends will reign in the marketplace. Additionally, we may be unsure which path we want to take, or which path might be most satisfying. 

What if you didn’t have to choose between being a generalist or specialist? What if you could combine elements of both into your work? For example, it sounds like your interests are more specific—art, film, and working on projects that are longer in duration. Perhaps this could give you a foundation for how you want to pitch yourself as a freelancer. I’d encourage you to sit down and brainstorm all of your interests. Once you have that list of things you enjoy and are curious about, that will give you an idea of areas, topics, and interests you may want to focus on within design. 

What if you didn’t have to choose between being a generalist or specialist? What if you could combine elements of both into your work?

However, when it comes to your approach and skill set, each project you work on allows you to add more experiences to your résumé as a graphic designer. Even if you use one approach or skill more than another, it’s okay to continue to keep the others in your toolkit for when you might need them. In this way, you are continuing to push the boundaries of what you know and what you can do for future opportunities. Again, brainstorming can help you gain more insight into what skills you possess and what skills you might want to develop further. I’d suggest setting aside 15 to 20 minutes to write down a long list of every skill you possess, whether learned in school or formal training or learned through experience on the job. All of these skills can be drawn upon and, if needed, you can dive deeper into this skill or that skill (beyond a generalist) to strengthen focus and specialize if and when the job calls for it. 

Right now, you are a graphic designer who has most recently worked in film. You said you had no prior experience in film before being hired as supervising art director on Midsommar, but there was certainly a reason you got the job—and it wasn’t just being lucky! There were skills you brought to the role that qualified you for the job despite what you see as lack of experience. Think about that role: What about your previous experience as a designer lent itself to you as an art director? In other words, identify the transferable skills or overlap between the two roles. What skills did you add to your repertoire as a result of taking on a new role? And what skills did you deepen? Now, think about why you really loved this role? What was satisfying about it? And how can you do more work that satisfies you in those ways? Perhaps it means pursuing more film-related work. Or perhaps not. Regardless, you now have this experience to draw on and highlight when talking with potential clients. 

You note that you enjoy moving around rather than doing the same thing over and over again. That’s important to know about yourself. That gives you flexibility, which you can choose to view as an obstacle or an asset. As an asset, it allows you to try new kinds or work, collaborate with a variety of clients, and continue to grow and challenge yourself. It seems like you see it as an obstacle because it might discourage specialization. However, there is room for both specialists and generalists in this world. It’s a matter of knowing which you lean toward right now and finding opportunities that match your approach. 

That said, if you come across an exciting work opportunity that requires specialization, you can always dive deeper and specialize for a period of time without losing your generalist skills. In fact, as you continue on your path, you might find yourself drawn to a particular niche. If so, go for it. Explore it. See what opportunities might come out of it. Who knows? You might find yourself on a thrilling new path that satisfies you in unexpected ways. And yet, if you don’t find yourself drawn to a particular niche, that’s okay, too. What I’m really saying here is that it’s your choice if you want to specialize or take a more general approach. Everyone is going to have an opinion, but it’s your career. You get to decide!

A few weekends ago I saw an incredible art exhibit of Bridget Riley’s work at the National Gallery in Edinburgh and there were several quotes from the artist in the handout. I think this one applies to your current questions: “The working process is one of discovery and it is worth remembering that the word discovery implies an uncovering of that which is hidden.” Right now, the answers feel hidden from you. You want to know which choice is the “right” one. But you’ll get there, step by step. In the same way a project you work on is a process and takes shape over time, your career path is the same. 

In the same way this experience led you to reconsider what’s next, you’ll continue to have more experiences in the future that will open doors you didn’t realize were even there. And as that happens, the questions you’re asking now about your future will change.

You don’t have to choose one thing, but you’re right in saying that you can’t do everything. Maybe now is the time to pick a handful of interests and skills that you want to deepen as you move into the next phase of your career. 

You’re asking a lot of questions right now—the role on Midsommar seems to have opened up new possibilities and that is wonderful. I am excited for you! In the same way this experience led you to reconsider what’s next, you’ll continue to have more experiences in the future that will open doors you didn’t realize were even there. And as that happens, the questions you’re asking now about your future will change. 

With that in mind, the most helpful question is, What is next? Do you want to pursue film more? If so, perhaps you have connections from your time working on Midsommar and could reach out to them about opportunities. Or do you want to take elements from your experience working in film and apply them to graphic design? Think about this next season of your work and what you want for it. Now you are a graphic designer who has art directed for film and you are a film art director who knows how to do graphic design. You don’t have to choose. You can encompass both.

To being both,

Coach Tina


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Asking Not Asking is a bi-monthly column written by Tina Essmaker, a New York City-based coach, speaker, and writer who helps others live into their possibility. To be considered for the column, send and email to with a short note about where you're at and where you want to be, and make sure to include the following: 

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