Tuesday, April 07, 2026

Break Now, Fix Later

 

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

What No One Tells You About Life After Work (and Why Your Old Playbook Won’t Save You)

Your post-employment days are likely to be much longer than you might think.

EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1

Apr 7, 2026

 

One of the great quotes from the writer and podcaster Gretchen Rubin is that “the days are long, but the years are short.” Every day may seem like a dreary Sisyphean struggle, but then one day you wake up and you’re carrying a cardboard box of your belongings out of the building and on your way to whatever’s next. Whether you want to admit it or not, for millions of us, retirement—whether voluntary or otherwise—is much closer than we imagine and now’s the time to start thinking about it.

I’m not talking about anything relating to financial matters, buying cheap life insurance, or whether it’s wise to have a will. You can see ads for those concerns everywhere you look. I’m talking about making some plans and decisions about how you’re going to spend your post-employment days which—in somewhat of a mixed blessing way—are likely to be much longer than you might think.

For better or worse, we’re living much longer these days, although the quality of life in those bonus “golden” years is an entirely different question. This longevity is largely because we’re paying much more attention to our diets, we’re exercising more regularly, the meds and medical treatments available to keep us alive are far more powerful and effective, and only the morons are still smoking and/or drinking too much.

Having lived through this transitional process several times and talked with dozens of others who are similarly situated, I have a few ideas and suggestions, warnings and words of encouragement, and other observations which I hope will be of value to you as you start to give some serious thought to an increasingly uncertain and challenging future.

First of all, try to avoid squandering your savings, severance and social security payments (such as they may soon be) on a startup or in buying a quaint neighborhood business that you’ve always liked and frequented. You may think you’re ready to roll up your sleeves, do whatever it takes, and jump back into the game, but the game has changed radically in many ways and you’re most likely not up to the task. And if my list of perils isn’t persuasive enough, try filling out a loan application or a new credit card app and putting the words “unemployed” or “retired” on the form. The word “retired” on a loan app is like a bright red stop sign for lenders—even at your own bank—and the pitiful excuses they give you are even more depressing.

Second, don’t try to teach anyone younger than 35 anything. It doesn’t matter whether it’s a bunch of high school kids who really don’t care, college students who simply can’t be bothered, or MBAs in grad school who think they already know everything. You probably don’t have the patience to deal with their lack of patience, the thick skin to deal with their arrogance, or the disposition to put up with their indifference and laziness. Worse yet, if you try to instill a little rigor or discipline, it’s like walking on eggshells among a bunch of snowflakes. It turns out too often that you’re the nasty ogre who just doesn’t get it. Teaching exec education courses is a slightly safer path, but even there no one is really interested in paying a ton of money to hear you rehash your old war stories.

Third, don’t expect or try to replace your prior earnings. That’s a pipe dream. It’s an employers’ market and there are dozens of over-qualified and out-of-work candidates chasing the same slots and opportunities. Sadly, it’s often a race to the bottom in terms of salary or other compensation and it rarely includes health insurance or other fringe benefits. It takes an especially strong stomach to settle for something which you regard as beneath your abilities and experience and it’s even more painful when you end up reporting to supervisors and managers who may be younger than your own grown kids.

Fourth, most of your technical skills are going to be regarded as anchors to the past rather than valuable tools. Look for jobs that take advantage of your negotiating experience, social skills, and storytelling ability. These may be the most satisfying positions anyway because you won’t be spending your days in a race trying to catch up with constant technological changes and dealing with patronizing nerds who are half your age.

Fifth, get comfortable with answering the omnipresent question: what are you doing now? Men and women who have worked hard and successfully for decades have a great deal of difficulty answering this inquiry without being embarrassed in one way or another. If you’ve retired after 40 or 50 years, be proud of that and understand that it’s perfectly fine to say either that you’re doing “nothing” or that you’re “looking” for what’s next. You’ve earned a break and some time off and there’s nothing to be ashamed of or any obligation on your part to be rushing around trying to get back in the saddle.

And finally, remember that it’s a great time to get back in touch with your kids, grandkids, and old friends you haven’t seen lately. You never know how much time you have left and no one’s kids ever said, “we wish he’d spent more time at the office.”  

 

Monday, April 06, 2026

Frank Bruni

 


We’re supposed to give students a map. I don’t even know the terrain.

It’s sweetly customary for college students filing out of a seminar room or lecture hall to thank the professor who has just finished jabbering at them, as if all that verbiage were a favor rather than a job. I’m amused by it and grateful for it every time.

But my students this semester often murmur something else as well.

“That was depressing,” one student said — not rudely, not as a complaint, but as an accurate summary of a discussion we just had about all the falsehoods and fury that thrive in the digital age.

“Another uplifting class” was another student’s sarcastic review of a conversation about the volume and variety of President Trump’s litigation against news organizations, whose economic and reputational woes are exacerbated by his attacks.

Clearly, some adjustments are in order. But how do I describe this troubled world of ours — the grave crossroads we straddle, the mighty stakes of our decisions — in a manner both truthful and gentle? How do I gird my students for the uncertainties and obstacles ahead while equipping them with an ample store of hope?

I’ve been on the faculty at Duke University for five years now, and this past one has been the most challenging and the strangest by far.

That’s not about Duke. It’s about higher education. It’s about America. It’s about dynamics — chiefly, this country’s tilt toward authoritarianism and the rapidly accelerating advances of A.I. — that render our tomorrows even hazier than usual. None of us knows what we’re in for and up against, and that confusion crystallizes on college campuses, which are by definition gateways to the future. They’re supposed to leave students with maps, routes, a destination. Not with compasses whose needles gyrate this way and that.

For much of the past decade, college students flocked to computer science, wagering that few majors were surer on-ramps to employment. A.I. has exploded that roadway. I teach in Duke’s school of public policy, where many students point themselves toward jobs in government or nonprofit groups. The ax that fell in the first months of Trump’s present term deforested that landscape.

Those are just examples, and this is hardly the first generation of young people to face disruption and major economic shifts. I can’t say just how unusual, in a historic sense, the unease that I feel around me is.

But I can tell you that my previous nine semesters at Duke are no rival for this one when it comes to the number of students who initiate conversations about what they should do next, what they should expect after that, where the country is headed, whether they’ll have any real say in that. I can tell you that their miens are darker, their voices more tremulous. I’m like a Magic 8 Ball who won’t — who can’t — disgorge the desired answers no matter how tightly it’s clutched, how vigorously it’s shaken. One of my faculty colleagues said recently that he’d never felt so inadequate as a mentor. Same here.

And we are both dealing with an extraordinarily lucky group of young people talented, driven or connected enough to breach the sanctum of a highly selective university whose resources and range of course offerings rank it among the nation’s best schools. Still, their advantages can’t compete with their apprehensions.

They’re undoubtedly picking up on their elders’ anxiety. We’re trying to manage not only their fears and bafflement but also our own. News stories about universities since Trump returned to the White House focus on huge funding cuts for research, which have led to painful belt tightening at Duke and other schools; on investigations into admissions practices and incidents of antisemitism; and on fines, more or less, for institutions at odds with Trump’s agenda. But the Trump administration’s impact on campuses has been more sweeping than that.

There’s a nagging sense of being surveilled by invisible eyes. No one wants to draw the White House’s ire. So some of us deliberate how carefully we should watch our language, avoiding “diversity” and “equity” and the Trump administration’s other dirty words. Some of us go out of our way to make our receptiveness to a broad spectrum of ideologies clear and not to play into progressive caricatures. But which adjustments are reasonable corrections of past mistakes, which are defensible self-preservation and which are cop-outs?

And what’s my purpose? A.I. isn’t just upending the job market; it’s raising questions about the necessity and utility of an array of skills. I teach writing, which is increasingly being outsourced to bots. Some are scarily adept at it. So should I pivot to bot maximization? Should other professors in other disciplines?

But what puzzles me even more is how to respond to a concern wisely articulated by Robert Pondiscio, a former public school teacher who is now a senior fellow at the American Enterprise Institute, in several essays and in public remarks. He has been sounding an alarm about “the unbearable bleakness of American schooling,” a trend that predates Trump’s political ascent and that the president and his compatriots have used as populist fodder.

“If you simply listen to the stories we tell students,” Pondiscio wrote in a newsletter late last year, we promote “a view of the world in which everything is broken, corrupt, dangerous or doomed.” But optimism, he argued, is an essential civic virtue. “No society can expect its children to engage with a world they think has already given up on them.”

This world hasn’t. If I’ve given my students the opposite impression, I’ve screwed up. I need to communicate that for all this country’s current trials, it still brims with opportunities, its promise greater than its woes. And a blurry future isn’t the same as a bleak one. It just asks today’s college students to be especially nimble and patient. And it demands that those of us who stand before them work extra hard to find an honest balance between uncomfortable reckonings and reasons not to despair.



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