40-Something Creatives: What Should We Do Next?

Five steps to help determine what we should do for the rest of our lives

Image: Alexander Milo

I get a fair amount of inquiries from my former colleagues and industry friends about what they should do next. They range in age but I’ve been particularly surprised by how many in their late 30s and early 40s reach out to me seeking perspective. And this has increased in the past twelve months noticeably more so than in the previous several years.

Several factors are at play here. A, It’s a function of myself getting older (although I’ve been in denial about this for the past two decades), and B, the creative and technology industries are changing so drastically. The pandemic has accelerated and generative AI is exacerbating these changes so much more quickly than anyone anticipated that the future is murkier than ever before.

Many of us have good, established careers and positions in our respective fields and companies. Some of us have or have had “executive director,” “VP,” “managing director,” etc, in our titles. A few of us are or have been even chief ___ officers at very respected companies.

20s, 30s, 40s

We thought we deserved the VP or the Creative Director titles in our 20s. We thought we deserved higher pay. We thought that the grass would be greener on the other side. We thought that there would be work that was meant for us and we were meant for them.

We worked hard. We jumped ship. We got those titles, promotions, and money. We thought that we had more time to figure out what to do with work and life.

And then, as we approach our late 30s and early 40s, one inevitable question seems to creep up on us. It’s a much trickier question to answer than before: What should I do next?

It’s trickier because when we reach our 40s, there aren’t going to be that many “nexts” left in our careers. It’s also more difficult to keep jumping ship in our 40s every two years than in our 20s or even 30s.

This question also weighs heavier on us because “next” could imply “for the rest of my life.” That’s a daunting thought.

When we were in our 20s, we still had more than 30, or even 40 years to go in our careers. It was ok to not know where we wanted to go in life or not have figured out life. It was ok to change course or to meander. There was a lot of time left “in the rest of my life.”

In our 30s, we encountered opportunities to lead, make more money, and move to new places. Some of us were promoted quickly, quicker than we (ok, I) should have been. We also started raising families and paying mortgages. We also became a little cynical about our industry. But it was ok. We were making good money. There were also starting to be more job options than there used to be. In addition to design firms and agencies, consultancies and in-house agencies started to hire us. And even more money came. With that, our expectations for our own lifestyles rose without us noticing.

As we get older, we collect various financial responsibilities in the forms of families, mortgages, cars, vacations, etc. Some of these aren’t responsibilities but rather, luxuries we bought into and lifestyles we got used to. Work is a job you can quit but family is work you can’t quit. We could technically quit our lifestyles but are we willing? Not so sure.

These financial responsibilities could hold us back. And if we have some wrinkles in life as I do, such as shared custody of kids due to a divorce (another topic to write about if I shed enough of my ego), our professional decision has much, much bigger consequences and implications.

Another realization that we denied for a long time: all of a sudden, the big Five-O is not that far away. As we watch our parents grow older, retire, and become more dependent on us, those futures for ourselves become more real. Yet, in our 40s, we aren’t quite old enough to cruise control our way into the career sunset.

“A creative individual in their 40s” according to Midjourney.

Side note: I asked Midjourney to generate an image but was disappointed by the lack of diversity and I didn’t see myself in it. I wasn’t going to use this but I thought I’d share here. AI is grossly biased and that is a problem.

Relevance

Being experienced is a good thing but there are only so many executive or managing director roles to go around. We had the digital chops that everyone craved but that was more than ten years ago. What used to be our differentiator is not only something everyone now has but can offer more cheaply and quickly. Have we become too expensive?

Is this why we are seeing more posts on LinkedIn about “being set free from (insert Big Tech here),” and/or “spending more time with the family,” a recent euphemism as Brian Morrisey of

The Rebooting

put it in our recent conversation?

In addition, there is economic and technological pressure that could make us redundant or worse, irrelevant.

Does it feel like the pace at which technologies, and therefore, the world around us, move has substantially picked up, compared to two decades ago when we started our careers? Or are we reaching the cognitive threshold of learning new technologies? Do we just not have enough time for ourselves like we used to? Yes.

So, as creatives in our 40s, with all these responsibilities as well as changes around us that can render our creative skills and experiences unnecessary just with a few prompts, what the hell are we supposed to do?

Not knowing is where you start

Most people who reach out to me are quite open about the fact that they don’t know what they want to or should do next. Some even admit that they might be having a professional existential or identity crisis. I was, too.

When I get these inquiries, I tell them first that I can’t tell them what’s right or wrong for them. I don’t think I can nor should I provide the answer to “What should I do next and for the rest of my life?” Instead, I’m happy to share the thought process I went through, where I was/am trying to go, and what to do in life, with a caveat that it may not apply to most people.

My role often is just to have a chat over coffee, ask some questions, and hope that those questions might help them find what’s inside them already.

The same goes for you with this post.

1. Future: Visualizing our paths ahead

As I was reaching my 40s, I started to visualize various possible paths ahead, and here’s what went through my mind about each:

1. Continue where I was: “I am the chief creative officer of a renowned digital agency and I like my job. I’m proud of what I’ve been able to achieve here. I could continue helping build this company.”

2. Move to another creative agency: “I’m getting calls from headhunters about a similar job at other agencies. They need some fresh blood to come in and turn things around. I’ve been able to learn about leadership, business, management, and finances here for the last 10 years. I could deploy my skills and experience to help someone else.”

3. Big Tech: “I’m also getting calls from Googles, Apples, Facebooks of the world. Many of my friends are jumping ship to tech. Money seems also nice. I may be able to retire if I stay for a decade.”

4. Start my own thing: “I’ve always been curious about what it’s like to start my own company and run it. Also, things are changing around me. I need to evolve and change.”

I do realize that I was fortunate to have these paths as my options.

Paths 1, 2, or 3 felt more secure. They also meant more money and stability at least for the foreseeable future. However, they felt predictable, for better or worse. I could see the next twenty+ years of my career in front of me at whatever company that I would work for. That kind of scared me.

Path 4 was by far the most unpredictable and the least secure. To go from having a paycheck one day to nothing when we have a family to feed in one of the most expensive cities in the world would put a LOT of strain on ourselves if we are the main breadwinner. With this unpredictable path, though, I couldn’t really see what lay ahead. To me, that meant I could potentially carve my own path. That felt exciting.

Then I asked myself these following questions. Not necessarily in this order at the time when I was trying to figure things out but this would be the order in which I recommend you interrogate these questions.

2. Self: “What’s really important to ME?”

As I wondered about the next 10, 20, or more years of my career, I started to make a mental list of things that were important to me.

• I want to have a positive impact on the world.

• I want to be in more control of my own destiny.

• I want to be able to provide a decent life for my family.

• Money is nice but it doesn’t buy me happiness.

• I like making things. The Work.

• I’ve always challenged myself, which led me to places I didn’t know I could go.

• When I’m 80 years old, I want to be able to say “I did it.”

I’m making it sound simple here but mind you, this internal debate took place over the course of a couple of years. The decision did become clearer for me after going through this exercise.

By the way, I will say that starting your own company is liberating but it isn’t for everyone. This post is not about that, and perhaps another topic to write about.

After several years of mental meandering, this is the question that I kept asking myself about the rest of my professional life:

“What’s really important to me?”

This is usually the one and the first question that I pose to my former colleagues and industry friends when we chat about their possible futures. We need to ask and keep asking this question ourselves over and over.

3. Place: Where do I want to live?

This was a constant topic of conversation between my wife and I for quite some time. Eventually, we decided New York City (or the vicinity) was the place where we wanted to spend the foreseeable future for both of our respective careers and lines of work we do (my wife is a life career coach), and for our kids and their education/life experience.

Having recruited many people in the US, Europe, and Asia, many people would say geography didn’t matter to them and would follow good work. That’s not true. It always matters greatly even if you don’t have kids. We need to really scrutinize this question and make a decision on this before we make a career decision. If we aren’t happy with where we live, we aren’t going to be happy with where we work.

If we have kids, what kind of education we want to provide for them, particularly for middle and high schools, is a huge factor and you need to settle this topic with our spouse.

This question helps prioritize our life and family decisions and that helps in narrowing our options.

4. Work: What kind of work do I really want to do?

As creatives, we like making stuff: The Work.

The best creatives I respect—and I mean creatives in a wider sense including designers, architects, artists, musicians, writers, builders, developers, etc—are the ones who keep making The Work. I find them inspiring. I also like helping other people do better work. I take joy in seeing others be able to make The Work that they might not have done on their own.

However, it’s possible that we might not see our futures as an extension of the previous two decades of our careers.

I will say that being in our 40s isn’t too late for a career change. That is, as long as we are willing to take roughly two years of a transition period to learn about ourselves and gain new skills. During this period, we need to discuss with our partners, particularly about money, and work together to make ends meet (see below).

Once we go through this transition, the rest of our lives—as individual professionals and as life partners—will be much more liberating and possibly more fulfilling.

5. Money: How much do you really need?

Money is a tricky thing. One of my family members told me in my 30s that I didn’t seem happy as I was making more money. I realized that more money didn’t necessarily give me real happiness.

Also, whenever I made decisions based on or heavily influenced by money, I always regretted my decisions. This was true for both my personal decisions as well as management decisions.

Like Place, it’s something we need to have an honest conversation about and to see eye to eye with our life partner. It can get uncomfortable at times. If not, we will end up paying the price. I did.

Having more money could benefit us in various ways. But be aware that it could also be crippling, especially in our 40s.

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To summarize, here are the five steps I went through:

1. Future: Visualize my possible paths ahead

2. Self: Ask what’s really important to me

3. Place: Decide with my partner where to live

4. Work: Search for joy in The Work or commit to a career transition

5. Money: Make money work for me, not the other way around

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