I recently had an article published in The i Paper, a UK national newspaper, about my experience “unretiring” after nearly two years of retirement, and then re-retiring, happier than ever. If you haven’t read it, that piece tells the full story of what I thought I was missing (socialization, challenge, collaboration) and what I discovered I actually needed.
What the article doesn’t get into is the part of early retirement that nobody really prepares you for: doing it while you still have kids at home.
Most retirement content (books, podcasts, financial planning guides) is written for people whose kids have left the nest. The vision it sells is the same as the one I had going in: extended travel, leisurely mornings, and complete control over your calendar. You do get some of that. But it’s just not the whole picture when you have to get someone to dance at 6pm.
Here’s the real version of what early retirement looks like when your kids are still very much part of the daily equation.
Retiring with Kids: The Vision vs. The Reality
My mental image of early retirement involved a lot of open-ended travel. Long trips to places that don’t fit neatly into two weeks of corporate vacation days. The kind of travel that my parents, who are currently in Australia, get to do now that their kids are grown. They can go anywhere, for as long as they want, with absolutely no school calendar to work around. They have the version of retirement a lot of us imagined…because they waited until 65 to retire.
I have a slightly different version.
With four kids in a blended family, each with their own school schedules, activities, and very strong opinions about their own lives, “extended travel” is almost non-existent. Summer has some flexibility. Long weekends give us no advantage over those that are still working — you can still take off. The school year is largely the school year, and the school year, unless you are homeschooling, still dictates our lives.
I forgot about this when I retired early and it’s really cramping our style. It’s a big constraint. I focused entirely on all of the extra time I could have with my kids when I retired and forgot that they are largely absent from our home most of the day. Wah. Wah. And not every teenager (i.e., none of them?) wants to spend a bunch of time with their newly-retired parent.
We do have a little bit of extra flexibility, but we need to be OK with bending the rules a bit. I took my older daughter out of school last year to hike the Inca Trail with me. But, the more advanced and AP classes they have, the harder it gets to remove them from school for an adventure without stressing them out.
How Do Working Parents Do This?
On the other hand, there are some distinct advantages to being retired and having teenagers. Their schedules don’t always align with work schedules. Let’s look at Exhibit A: Sports Tournaments.
Baseball tournament season in Wisconsin means travel and 3-4 day tournaments at least a few weekends over the spring or summer. Teams arrive Thursday or Friday, then play all day typically Friday, Saturday, and Sunday. The whole weekend, essentially, is consumed by a single activity. We only had a couple this year which we split with my husband’s ex-wife, but it was still a lot and left me wondering: how do the working parents do this?
No, seriously. How do you do this? I know not all of you have flexible jobs like I did. Plus, you’ve worked a full week, you’re ready to relax or run errands, and by the end of this tournament, you have no weekend left. I can’t figure out where the recovery time goes, or where you find the space to do anything else you care about.
I retired partly because I wanted time back. The kids have made it clear that some of that time belongs to them. But at least I’m not also fighting a full work week for what’s left. That formula doesn’t add up and I don’t take my extra time for granted.
What Retirement With Kids Actually Looks Like
Here’s what my days actually look like, now that I’ve recalibrated my expectations away from “continuous European travel” and toward something more realistic:
Get up early and work out (so far, nothing has changed here). Write, then get some work done for my Capstone class. Have lunch with my husband, then walk. Perhaps some more University work or tasks. Tea time at around 3pm with a book. A few more things, then BAM! Various kids come home, I drive one somewhere. Someone makes dinner. I pick them up. Sometimes I’m out driving people around multiple times. Sometimes there’s a game or a meet. And, sometimes, I get to rest on the couch and read or watch TV. Usually not. I get tired at a time that approaches what a traditional retiree would consider bedtime. Then I go to bed and do it all again.
My parents, from their hotel in Cairns overlooking the water, represent the retirement I’ll eventually have. I represent the retirement that’s available right now, with the life I have rather than the life I imagined. And it turns out that retirement is still significantly better than working full-time, even with the school calendar and the tournaments.
The Pros: What Retirement Gets Right Even With Kids Around
You are present in a way you couldn’t be before. I’m generally home when my kids are home. I can go to more activities. And I’m not distracted as much by the things happening at work.
You can absorb the chaos without it breaking you. Four kids, blended family, multiple households, multiple schedules, multiple sets of needs. It is quite a lot. When I was also managing a full executive workload, this level of family complexity was too much. Now I have more bandwidth for it. It’s still insane, but it’s a better kind of insane.
The logistics of parenting become more manageable. Appointments, school events, teacher conferences, pickup when someone is sick: these are the small grinding logistics of parenting that fall through the cracks when both parents work full-time. I can do these things now. I can be the one that shows up at school when a kid breaks an arm. (True story, I had to meet my husband and daughter at Urgent Care the day she broke her arm at recess because I was working.)
Your relationship with time changes. Even with the school calendar constraining travel, I have a fundamentally different relationship with my days than I did when someone else owned most of them. I don’t like to do back-to-back-to-back anymore. And I feel like I have a better life balance than ever before.
The Cons: What’s Still Hard
The travel vision is on hold. I want to mention this because I don’t think enough people talk about it. The extended, untethered international travel that many people imagine as the centerpiece of early retirement is largely not available to me right now. We like the schools the kids are in and while I am working on a plan to move abroad, it gets logistically difficult when dealing with ex-spouses and blended families.
The school calendar owns significant portions of your year. September through June, the rhythm of the week is set by school and activities. Summer has more flexibility, but summer is also sports season.
You can feel the gap between your freedom and everyone else’s. This is the subtle one. On a Tuesday morning when you’re hiking and most of the world is in meetings, retirement feels like exactly the right choice. On a weekend when both days are consumed by activities, the freedom you thought you’d have feels a bit hypothetical. That gap between expectation and reality takes some adjusting to. You also have a harder time finding friends to hang out with during the week because they are still working.
The “why aren’t you working?” question comes from unexpected directions. People in the United States don’t really understand early retirement (not most people anyway). People are either skeptical or jealous or trying to get me to come back to work or skeptical and secretly jealous. We get questions from other parents at activities and well-meaning relatives, and sometimes I don’t have great answers about what I’m doing with my time. I’m relaxing, ok? I’m reading. I am recovering from the burnout you still have. I am changing the world with my attention and choices. Early retirement is still unusual enough, and the financial independence movement obscure enough, that you sometimes have to explain yourself in contexts where it would be easier not to. So sometimes I just say, “I’m on sabbatical” and leave it at that.
Is It Still Worth It to Retire Early, Even With the Kids Around?
Yes. The answer to that question is undeniably yes. I don’t have the retirement my parents have right now, but I do have unprecedented freedom that most 40-somethings don’t have. The kids are growing up, and the school calendar that currently shapes my life will, before long, be someone else’s constraint.
What I have now is something just as good: the freedom to be present for the years that go faster than you think. Yes, the activities are exhausting. They’re also, viewed from a certain angle, exactly the kind of thing I retired to have time for.
Not every day looks like the retirement I imagined. But life is still, without question, better than the alternative.
I wrote about my unretirement and re-retirement experience in The i Paper. Here, you get the full story of what I thought I was missing and what I actually found. And if you want to talk through what early retirement might look like for your own situation, coaching is available.



