How To Decide What To Do Next
Five steps to help determine what we should do for the rest of our lives
“20 years of experience. In my 40s. 2 kids. Unsure what to do next. What should I do?”
An old colleague of mine asked me. I wrote my take in a benign LinkedIn post and it struck a chord.
I get this question from former colleagues and industry friends of various ages, especially in their late 30s and early 40s seeking perspective. This has noticeably increased in the past 24 months compared to previous years.
Several factors are at play. A, It’s a function of getting older, and B, the creative and technology industries are changing drastically. The pandemic has accelerated and generative AI is exacerbating them so quickly that the future is murkier than ever.
I wrote this piece in July 2023, and it’s still relevant. This week, I’m posting a revised version.
20s, 30s, 40s
In our 20s, we thought we deserved the VP or Creative Director titles, higher pay, and that the grass would be greener elsewhere, with work meant for us and us for them.
We worked hard, jumped ship, and got titles, promotions, and money. We thought we had more time to figure out work and life.
As we approach our late 30s and early 40s, one inevitable question arises: What should I do next?
It’s trickier because by our 40s, there won’t be many “nexts” left in our careers. It’s also harder to switch jobs every two years than in our 20s or 30s.
This question weighs heavier on us because “next” could imply “for the rest of my life.” That’s a daunting thought.
In our 20s, we had over 30 or 40 years left in our careers. It was okay to be unsure about our life direction, to change course, or to meander. There was a lot of time left.
In our 30s, we encountered opportunities to lead, earn more, 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 became cynical about our industry. But it was fine. We were earning well. More job options emerged. In addition to design firms and agencies, consultancies and in-house agencies started hiring us. More money came. Our lifestyle expectations rose without us noticing.
As we age, we collect various financial responsibilities in the form of families, mortgages, cars, and vacations. Some are not responsibilities but luxuries and lifestyles. Work is a job you can quit, but family is work you can’t. We could quit our lifestyles, but are we willing? Not sure.
These financial responsibilities could hold us back. If we have life wrinkles like shared custody of kids due to a divorce (another topic if I shed enough ego), our professional decision has much bigger consequences.
Another realization we’ve denied for a long time: 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 old enough to cruise control our way into the career sunset.
Not knowing is where you start
Most people who reach out to me are open about not knowing what to do next. Some admit they are having a professional existential or identity crisis. I was, too.
When I get these inquiries, I tell them I can’t tell them what’s right or wrong for them. I can’t provide the answer to “What should I do next and for the rest of my life?” Instead, I’m happy to share my thought process, my goals, and what to do in life, with the caveat that it may not apply to most people.
My role is to chat over coffee, ask questions, and hope they help them find what’s inside them. The same goes for you with this post.
Having gone through the process myself, this is the sequence of questions that I ask when figuring out what to do next.
1. Paths: Visualizing our paths ahead
As I approached my 40s, I started to visualize various paths ahead. Here are my thoughts on each:
Continue where I was: “I’m the chief creative officer of a renowned digital agency and I like my job. I’m proud of my achievements here. I will continue helping build this company.”
Move to another creative agency: “I’m getting calls from headhunters about a similar job at other agencies. They need fresh blood to turn things around. I’ve learned about leadership, business, management, and finances here for the last 10 years. I could deploy my skills and experience to help someone else.”
Big Tech: “I’m getting calls from Googles, Apples, Facebooks. Many friends are switching to tech. Money seems nice. I may retire if I stay for a decade.”
Start my own thing: “I’m curious about starting and running my own company. Things are changing around me. I need to evolve.”
I was fortunate to have these paths as my options.
Paths 1, 2, or 3 felt more secure. They meant more money and stability for the foreseeable future. However, they felt predictable. I could see the next twenty+ years of my career at whatever company I would work for. That scared me.
Path 4 was the most unpredictable and least secure. If we’re the main breadwinner, going from having a paycheck one day to nothing in one of the most expensive cities would strain us. With this unpredictable path, I couldn’t see what lay ahead. That meant I could carve my own. That felt exciting.
2. Self: “What’s really important to ME?”
As I contemplated the next 10, 20, or more years of my career, I started to make a mental list of what was important to me.
I want to have a positive impact on the world.
I want more control of my destiny.
I want to provide a decent life for my family.
Money is nice, but it doesn’t buy happiness.
I enjoy making things. The work.
I’ve always challenged myself, which has led me to unexpected places.
At 80, I want to say “I did it.”
I’m simplifying here, but this internal debate lasted a couple of years. After this exercise, the decision became clear.
Starting your own company is liberating, but it’s not for everyone. This post isn’t about that and is another topic to write about.
After years of mental meandering, I kept asking this question about my professional life:
“What’s really important to me?”
I ask my former colleagues and industry friends about their futures. We need to keep asking this question ourselves.
3. Money: “How much do I really need?”
This is the most crippling factor for many of us. Not because we don’t have enough money but because we got used to the comfortable lifestyle that it afforded us.
In my 30s, a family member told me that I didn’t seem happy despite making more money. I realized that more money didn’t guarantee real happiness.
I regretted decisions based on or influenced by money, both personally and in management, whenever I made them.
We need to have an honest conversation and align with our life partner. It can get uncomfortable, but otherwise, we’ll pay the price. I did.
More money could benefit us, but it could also be crippling, especially in our 40s.
4. Place: “Where do I want to live?”
My wife and I often discussed where to live. Eventually, we decided on New York City (or nearby) for our careers (she is a life career coach) and our kids’ education/life experience.
Having recruited many people in the US, Europe, and Asia, I’ve heard so many candidates say geography didn’t matter and would follow good work. That’s not true. It always matters greatly to everyone, especially those without kids. People with kids are willing to compromise on geography. Single people? Not as much as they think they are willing.
We need to scrutinize this question and decide before making a career decision. If we aren’t happy with where we live, we won’t be happy with where we work.
If you have kids, a huge factor is what kind of education you want for them, particularly for middle and high schools. You need to resolve this topic with your spouse.
This question helps us prioritize our life and family decisions and narrow our options.
5. Work: “What kind of work do I want to do?”
I happen to be in the industry of making things. As a designer, I enjoy making the work.
What’s hard in our 40s and 50s is that what we enjoyed making in our 20s and 30s isn’t relevant anymore. So we have to figure out how what we know from our prior two decades can still be relevant in the world and applicable to different needs in business today.
In my case, my experience in simplifying, identifying problems and opportunities, coming up with ideas and visualizing them, and creating narratives and stories, turned out to be a useful skill for C-suites of various companies. That’s the kind of work I do now. I enjoy it and find meaning in it because I can make a difference that goes beyond my reach as an individual.
But some of us may not see our future as an extension of our past. You then may want to commit to a career change.
Changing careers in our 40s isn’t too late, as long as we’re willing to take a two-year transition period to learn about ourselves and gain new skills. During this time, we need to discuss with our partners about money and work together to make ends meet.
After this transition, the rest of our lives—as professionals and life partners—will be more liberating and more fulfilling.
To summarize, here are the five recommended steps for figuring out what to do next:
Future: Visualize your possible paths ahead
Self: Ask what is really important to you
Money: Make it work for you, not the other way around.
Place: Decide what city you want to live
Work: Look for joy in the work you do or commit to a career transition
This topic was also a conversation with one of the listeners of The Creative Mindset podcast that I host. Have a listen here:
Spotify:
Apple Podcast:
Excellent observations. Creating joy for oneself is paramount to fulfillment. Especially working in a lifetime of creative endeavors.
As a parent, designer/creative director and self analyser in my late 30's, I really enjoyed this read.
For creative professionals, self evaluating the balance between what you earn and what you create is essential. In fact, it's almost a hobby of mine to self asses and plot new goals every year. Of course, not everyone is in the fortunate position to have a choice.
A while ago, I read about an approach someone was taking through their life as 3 year cycles. 3 years making - learning to get the most out of your craft, 3 years in leadership - learning how to get the most out of others. I also found myself in this flow by chance. Getting this perspective is becoming more and more useful as changes in our world accelerate. The cycles will become shorter as creative tools becomes easier to use, I'm sure.
My north star is always to ask myself, "when I am old, what will I regret not having or doing?".