How I Would Futureproof Myself If I Were Starting Out Today
Author’s Note: thank you for the great responses last week to The Crossing the Rubicon Thanksgiving. For a couple of timely pieces from the Sunday Morning Post archives, check out Black Friday Isn’t What It Used To Be and Ben’s Holiday Gift Guide. Thanks for being here.
How I Would Futureproof Myself If I Were Starting Out Today
Today’s young people are entering one of the hardest job markets in recent history, and perhaps one of the toughest ever if recent trends continue to play out. Not only are employers not hiring aggressively right now because of their uncertainties about the economy, but AI is decimating the workforce needs in all types of occupations and industries. Clerical work, data entry, coding and computer science, customer service/call center jobs, even manufacturing jobs and warehouse work: barely any industry is “safe” from the impact of AI.
I know a lot of people in the technology ecosystem including futurists and freethinkers say that AI will be a great equalizer by helping lower skill workers compete with those who have more expertise and experience. Many people also believe, understandably, that AI tools will make workers more efficient and effective, thereby freeing us up to do more complex, meaningful work, or, even better, enjoy more leisure time.
There is a case to be made for both points. Just having ChatGPT proofread your emails before sending them out, for example, can help someone with poor writing skills communicate more effectively, and with fewer glaring typos. And certainly all the time saved from these data entry jobs that can now be done by AI frees up staff time for more meaningful work (although, to be fair, I know a lot of data entry-types who get the meaning itself from data being manually inputted correctly; their brains are just wired that way).
But, when all is said and done, I don’t buy the corporate altruism vision of AI, in which technology serves to usher the modern worker into some egalitarian wellspring of productivity and purpose. Corporate leaders might say the right things now about AI being a tool and their workforces being like families, but quickly, I believe, once the productivity benefits and cost savings of moving various tasks and responsibilities to AI are recognized, the workforce, broadly speaking, will go through the most sweeping changes since the Industrial Revolution or the beginning of the Computer Age. The earthquake we are about to go through may even be more significant than either of those transitions. It has already started, which if you are a regular reader of The Sunday Morning Post, you may have already read about here, here, and here, so I won’t dwell more on the overview of the landscape at the moment.
Futureproof Yourself
One of the founding catalysts for The Sunday Morning Post was reading a book called Futureproof: 9 Rules for Humans in the Age of Automation, by Kevin Roose (the subtitle has since changed to “9 Rules for Surviving in the Age of AI,” an interesting update since the book was first published in 2021). It was an impactful book when I first read it four years ago, and I have come back to it several times. It is recommended reading, for sure.
What Futureproof sparked me to think of was how I could differentiate myself in the workforce, and how I could add additional value by leaning into my specific skills like writing and synthesizing ideas. The Sunday Morning Post was a way to do that, and I am forever grateful to my employer for allowing me to keep writing these articles week after week.
I am 42 years old — no longer young, but with a solid 20-30+ years left of meaningful career. What I wanted to do today was share advice with those who are 20-25 years behind me in their own professional lives (or even those who are concurrent with me, or even some years ahead). So today’s topic is how I would Futureproof myself if I was just getting started out today (and knew some of the lessons I have gained in the past 20-25 years myself).
Principle #1 - Don’t Specialize
There is, of course, an old investment axiom about not putting all your eggs in one basket. The technical term today would be concentration risk. If you had 100% of your stock portfolio in Nvidia, for example, you’d be sitting extremely well right now, but you would also be carrying massive risks. Lots of General Motors workers, for example, got wiped out when the company went bankrupt in 2009, having put all of their retirement savings into something that couldn’t possibly go bust, and yet did.
From a work skills perspective, it is important to not be good at just one thing, because there is always a chance that that one thing could be made redundant or obsolete by a changing world. If you are particularly good at digital marketing, for example, you should also take business courses to understand budgeting and cash flow. If you are into something creative, learn about entrepreneurism, too. Maybe you won’t actually start a business of your own, but you’ll understand more about how industries work. The inverse of this is true too; if you are a business-type, it would be beneficial to be an expert on something completely different, or to be a creator of some kind. Maybe it is painting, cooking, writing — doing something that creates something new in the world is pretty empowering, too. And that’s not just a way to distinguish yourself in a career, but to live a full life.
When I was graduating from Harvard, many of my classmates were going to work in investment banking and consulting (I, on the other hand, taught adult education and worked for the Red Sox). But what I understood from speaking to many of my friends about their interviews was that the big New York firms were not looking for just finance majors; they were looking for finance majors with a minor in biochemical engineering, for example, or Near-Eastern studies or Spanish, etc. They wanted people who had a particular area of focus, but could look at the world through different lenses when necessary. So be a dual (or even a triple) threat.
One more quick aside on this principle: the trend in the NBA over the past ten years has been towards players who can dominate in different areas of the game. A team that plays with the traditional five positions (two guards, two forwards, one center) is becoming a relic of the past — players today are expected to be able to shoot, pass, dribble, and defend in all types of game scenarios and in all positions on the court. The best player in the NBA, Nikola Jokic, is technically a center for the Denver Nuggets. So far this season, he is getting 12.6 rebounds per game, which you would expect from a big man. He is also getting 11 assists per game, which leads the league, and is shooting 44% from three-point territory, which puts him in the Top 20 in the league in that category, which is unheard of for a center. Be like Nikola Jokic: extremely good at multiple things, and able to perform well in unexpected ways (he also loves horses).
Principle #2 - Develop Social Capital
Another old axiom is “it’s all who you know.” To many people, this smacks of nepotism and favoritism, disadvantaging those who lack family and community support, economic or otherwise. Fair. But before completely discounting the “it’s all who you know” concept, I would counter with another perspective: people like doing business with people they know and with people they like, so you have to get out there and get proximity to those with connections and influence.
Sure, it can be very hard to walk into a room without knowing anyone, or one that is made up of a crowd of people unlike oneself. It can be intimidating and even anxiety-inducing. But showing up is half the battle, as they say, and rapport is built through repeated exposure.
Every handshake, every coffee meeting, every volunteer role, every “Sure, I can help with that” becomes part of the fabric of connection that can lead to future opportunities. Skills matter, but relationships often open doors. And in an age when AI can outperform humans at many technical tasks, human connections will be one of the few moats that will remain. Cultivate relationships relentlessly, but do so authentically and with a servant’s-heart attitude, as no one likes a pushy, salesy, over-the-top networker who is just in it for themselves.
Much in the same way that it is good to have multiple skills in the workforce that you can lean into, it’s also good to be involved in purposeful activities that get you out of your normal work routine and put you into the community with others. For me, this was serving on my City Council and School Committee, as well as coaching my kids’ sports teams and volunteering in various other ways including through board service. Sometimes I feel guilty that I often get more out of these activities than I feel like I am putting in. This was never the reason why I participated in these things, but each of these activities has been good for my professional career, for sure.
Principle #3 - Be a Person Others Want to Work With. Embrace Being Human.
This may be the single most underrated career skill: to be someone others want to be around. The people who thrive over decades are not necessarily the smartest or fastest or the technically proficient, they are the people whose phone calls and emails others are actually happy to see. They are the people who show up prepared, say thank you, don’t hoard credit, and don’t make everything harder than it needs to be. The people who can be on-point and focused, but also cheerful and uplifting.
At least for now, being great to work with is almost impossible for AI to replicate. Humans still own that terrain (although I have my worries that AI chatbots — and perhaps actual robots — will own this space soon, too). But for now, being kind, reliable, and steady are all major differentiators in the workplace.
Related to this, the more the world automates, the more valuable the uniquely human skills become. Storytelling. Humor. Negotiation. Compassion. Curiosity. The ability to reframe a problem in a way that sparks understanding. Be the person who can read a room — who can sense when a colleague is struggling or when a team needs a morale boost. Be the person who listens more than they talk. Be the person who can explain a complicated idea in simple language. These are timeless talents that will only become more essential as the technical skills around us get automated.
As a quick bonus item in this category, I told my former assistant (who has since moved on to bigger and brighter things) that everyone has aspects of their job they don’t like — successful people just get them done. And, if you can figure out what your boss doesn’t like to do and get really good at those things, you’ll have quite a lot of job security. Help figure out how to get these things done, even if they are not a part of your job description.
Principle #4 - Embrace the Trades
Honestly, this principle could be its own full series of articles, and is worth more discussion and amplification. As more white-collar work becomes automated, the trades are entering a kind of renaissance. Electricians, welders, plumbers, mechanics, HVAC technicians, carpenters — these are extraordinarily hard fields to automate because they require improvisation, spatial reasoning, physical dexterity, and real-world problem-solving. We also have a massive shortage of these workers, with a “silver tsunami” of retirements taking place as older workers retire. The CEO of Ford said on a recent podcast that the company has over 5,000 vacancies for mechanics right now, despite the jobs sometimes paying up to $120,000/year.
Blue-collar jobs often pay well, and don’t always require a four-year degree. Many come with entrepreneurial upside: owning a small shop, hiring apprentices, building a business with a local reputation. Building a local monopoly in a key blue-collar industry can be quite lucrative (back to Principle #1 — be good at HVAC work, but understand the business side of it as well, and you can do really well).
If I were 18 today, I would not assume college is the best (or only) path. The trades are not a fallback. They are a strategic hedge against a future dominated by bots, screens, and algorithms.
Principle #5 - Develop a Side Hustle
One of the best things you can do for your future self is give yourself more winning chances through multiple rolls of a multisided die. If one part of your career faces disruption, another part may take off. You need to give yourself as many rolls of the dice as possible.
Side hustles are not only financially helpful, but they can build new skills and networks. They can help support you financially while you work through the ups and downs of a more traditional career path. They can also be a great creative outlet or a way to scratch an entrepreneurial itch.
Not every side project will turn into a full-time job. Most won’t, and some may not even be financially viable. But the point is not to build a unicorn; the point is to have healthy outlets, to give yourself some options, and to build resilience. The more paths you have open, the harder it is for a changing world (through technology or otherwise) to close them all at once. Remember, give yourself multiple rolls of those dice.
Just be mindful you are not pursuing a side hustle at the expense of a stable growth opportunity in a more traditional workplace, or that you’re not driving yourself nuts or spreading yourself too thin from working too hard at something that isn’t viable or shooting scattershot trying to find something that lands.
Summing It Up
If I were starting out today, I would not fear AI, but I would not be naive about it either. I would assume the world is going to change dramatically, and that many of the jobs that look stable today won’t exist in the same form in ten years.
But here’s the good news: the qualities that one should take to futureproof themselves today are not new. In fact, most of the principles I have noted above are old, ancient even. Breadth of skill. Depth of character. Strong relationships. Curiosity and creativity (even if you don’t consider yourself to be that creative of a person). The courage to reinvent and the willingness to try more than one thing are ways that help demonstrate adaptability in a changing world. I would start by getting out there and meeting people, and seeing where those conversations and those relationships lead. Develop skills and expertise in more than one area, and be willing to explore multiple pathways, traditional and non-traditional alike.
Ben Sprague lives and works in Bangor, Maine as a Senior V.P./Commercial Lending Officer for Damariscotta-based First National Bank. He previously worked as an investment advisor and graduated from Harvard University in 2006. Ben can be reached at ben.sprague@thefirst.com or bsprague1@gmail.com.
Our family gained a new member this past week. Meet Pumpkin, an early Christmas present for our three kids, and especially our youngest, who has been asking for a pet for quite some time. We are all smitten. Thank you to the Bangor Humane Society. Looks like we are cat people now.
Have a great week, everybody.