I’m Gen X.

I learned to type on a typewriter. Mistakes required White-Out.

I remember AOL discs showing up in the mail, the sound of dial-up internet, and waiting for someone to get off the phone so I could get online.

I remember when a car phone was a big deal—and when you tried to finish the call before the next minute started because every minute cost money.

Now I’m a financial planner, a father of four, and a member of the sandwich generation.

My parents are Boomers. My wife is a Millennial. My kids are growing up in a world where artificial intelligence may change what “having a career” means altogether.

And lately I’ve been thinking a lot about one question:

What exactly are we preparing our kids—and ourselves—for?

We’ve seen this movie before. Sort of.

Every generation has lived through technological change.

But AI feels different.

It isn’t simply replacing physical labor or making an existing process faster. It can write, code, analyze, create, diagnose, research and increasingly perform work we spent decades telling our kids was “safe” because it required an education.

Depending on whom you listen to, AI is going to create unprecedented abundance, eliminate millions of jobs, transform the workweek, solve problems we thought were impossible—or eventually decide humanity is unnecessary.

Somewhere between WALL-E and Terminator 2 is probably a reasonable place to start.

I don’t pretend to know which future we’re getting.

What I do know is that Gen X doesn’t have 30 years to wait and find out.

Gen X is standing in an interesting place

A lot of us are in our 40s and 50s.

These should be our peak earning years.

At the same time, we’re paying for kids, thinking about college, helping aging parents, staring at retirement 10 or 15 years down the road and wondering whether the career we built will look anything like it does today.

That’s a lot to carry even without AI.

Add layoffs, corporate restructuring, automation and rapidly changing skill sets, and I think the financial-planning conversation needs to change.

The question isn’t simply:

“How much do I need to retire at 65?”

It may be:

“How do I build enough financial flexibility that I have choices if my career changes before I’m ready?”

That distinction matters.

Maybe financial independence needs a new definition

For years, financial planning has largely treated retirement as the finish line.

Work. Save. Invest. Retire.

But what if the next 10–15 years don’t follow that neat sequence?

Maybe financial independence for Gen X isn’t about never working again.

Maybe it’s reaching the point where losing a job doesn’t create a crisis.

Where you can change careers.

Take six months off.

Start something.

Help a parent.

Spend more time with your kids.

Turn down a job you hate.

Or use AI to make yourself dramatically more productive rather than simply worrying that it will replace you.

That’s less about predicting the future and more about creating optionality.

You don’t have to predict the future. You need to be positioned for it.

I’m thinking about this inside my own business, too

I’ve been calling it Thrive 2030.

I’m looking at my own profession and asking the same uncomfortable questions I’m asking clients.

What should a financial advisor be doing five years from now?

What will AI do better than I can?

What should technology handle?

And, more importantly, what becomes even more valuable when technology can do almost everything else?

I don’t think the answer is trying to compete with AI at calculating a Roth conversion or producing a retirement projection.

The technology will get extraordinarily good at those things.

I think the opportunity is connecting all of it.

Taxes. Investments. Estate planning. Retirement. Career decisions. Aging parents. Kids. College. Insurance. Family experiences. And the inevitable trade-offs between all of them.

That’s where I think human advice gets more interesting, not less.

“All set” may not be enough anymore

I’ve seen families with millions of dollars who are objectively all set.

They have investments.

An estate plan.

Insurance.

Retirement accounts.

Maybe several advisors.

Every individual piece looks fine.

But nobody is asking whether all of those pieces are actually working together.

That’s the difference I keep coming back to:

All set versus optimized.

As the world becomes more complicated, I think that distinction becomes more important.

And it isn’t only about squeezing another percentage point out of something.

Sometimes optimization means taxes.

Sometimes it means helping your parents transfer wealth thoughtfully.

Sometimes it means giving your kids a better start.

Sometimes it means creating enough flexibility to survive a career disruption.

And sometimes it means realizing you can afford to stop optimizing the spreadsheet and go make a memory.

Which brings me back to my kids

One of my sons, Finn, loves baseball.

And like every parent, I can find myself looking way too far ahead.

What will high school look like?

College?

What kind of career will he have?

What skills will matter?

Will AI completely reshape whatever profession he eventually chooses?

Maybe.

But baseball has taught me something useful about that too.

We’re probably in the early innings of this AI transition.

Nobody knows what the ninth inning looks like.

And I’m not sure our job as parents is to perfectly predict it.

Maybe our job is to raise kids who can adapt.

Who are curious.

Who know how to communicate.

Who can work with people.

Who can solve problems.

Who can use new tools without becoming completely dependent on them.

And who understand that a career is supposed to support a life—not become the entire point of one.

The same may be true for those of us in Gen X.

Don’t skip 2026 worrying about 2050

I’m fascinated by AI.

I’m optimistic about what it could do.

I’m also realistic enough to know that it may create some painful disruption along the way.

So I’m going to spend a lot more time here talking about it: AI and the future of work, Gen X and job transitions, financial flexibility, the next 10–15 years, aging parents, launching kids, retirement and what all of this means for families trying to make smart decisions in a world that’s changing incredibly quickly.

Because those things aren’t separate financial-planning issues.

They’re one life.

And increasingly, they’re one family.

My parents’ generation is asking what to do with everything they’ve built.

My generation is trying to help our parents, launch our kids, navigate the most important earning years of our careers and still prepare for retirement.

Our kids may enter a working world we can barely imagine.

That’s the view from the middle.

And it’s increasingly how I think about financial planning.

Maybe Finn really will play center field at Fenway someday.

Maybe he’ll have a job that doesn’t even exist yet.

I have no idea.

But I know he’s 13 right now.

And I’m not going to skip this season trying to predict the ninth inning.

Enjoy the Ride.

Scott Nelson | Thrive Wealth Strategies

Securities offered through LPL Financial, Member FINRA / SIPC. Investment Advice offered through Flagship Harbor Advisors, a registered investment advisor. Thrive Wealth Strategies and Flagship Harbor Advisors are separate entities from LPL Financial.