What I Wish I Planned For My Family A Lot Sooner, According To 12 Dads


“Plans change,” as the saying goes. And life is full of plans. Plans for quality time, for raising good kids, for staying healthy, for teaching valuable lessons, for creating memories. Sometimes, everything goes according to plan. Other times, life throws your plans into disarray. The point of planning is to prioritize and plot out steps toward the future. Looking back on what you planned (or didn’t plan) will almost always reveal some regrets. But it also helps solidify priorities and perspectives now.

The fact is that we have moments when we look back and say man, I should’ve planned for that. Because of course we do. It’s only human. In hindsight, these 12 dads all realized they should’ve planned a bit more for certain things. Whether struggling to create financial security, allowing for meaningful shared experiences, or even planning too much and not being present enough, these men all admitted struggling with regret regarding what they could’ve paid attention to much earlier — but that realization led to sharper focus. Here’s what they wish they planned for, and what you should take away from their admissions.

1. I Wish I Would’ve Planned An Earlier Disney Trip

“By the time we decided to make it happen, our kids were in high school. Going to Disney with your family when you’re in high school, understandably, isn’t the most fun experience. Don’t get me wrong: we made a lot of good memories. But there were also healthy, healthy doses of complaining, sarcasm, and screen time. I remember seeing other families there, with little ones, and I envied that the tantrums they were enduring were mostly about being hungry or tired. I feel like the sweet spot for a vacation like that is when your kids are young enough to be swept up in all of the characters and magic. Planning that trip earlier would’ve been a better experience for everyone, I think. Hopefully we can make up for it by planning ahead to all go as adults.” — Garrett, 46, California

2. I Wish We Would’ve Planned A Family Reunion Sooner

“I regret not at least suggesting to plan an extended family reunion so my kids could meet their relatives from out of state, and out of the country. We had one when I was in middle school, and it was pretty awful. Kind of just a boring time with people I’d never met, telling me stories about stuff I’d never thought about. But as I grew up, for some reason, those stories and those people would pop into my head every now and then. I’ve never been a huge, ‘Stay true to your roots!’ kind of guy, but there was something worthwhile in the experience. If anything, it made me ask questions later on. Like, ‘Hey Dad, did Uncle So-and-So really get arrested for protesting?’ Stuff that, at the time, was overshadowed by the awkwardness of it all, but then became really cool and interesting as I matured. I wish I would’ve planned something similar to give my kids an experience like that.” — Daniel, 50, North Carolina

3. I Wish We Would’ve Planned To Teach My Kids More About Finances

“ From a young age, I would have involved them in simple budgeting activities, teaching them the value of money and the importance of saving. I’d have set up savings accounts for them, encouraging them to save a portion of any money they received, whether from allowances or gifts. This early financial awareness could have helped them make more informed decisions as they grew older, especially during their teenage years when they began to earn their own money. This early financial foundation would have prepared them for adult financial responsibilities and instilled a sense of discipline and foresight regarding money matters. Looking back, I realize this is a crucial life skill that I wish I had prioritized from childhood.” — Hashi, early 40s, Minnesota

“Not just the financial aspect of it, though that is a huge, huge deal. But the whole empty nest/saying, ‘Goodbye’ experience as well. Everything was just so, so rushed for both of our boys. And they’re close in age, so it was a situation where, as soon as we got one shipped off to college, the other was ready to go. We didn’t make any plans to savor the experience, and really prepare for what would be like – for all of us – after everything had settled. We didn’t have goodbye parties, or anything like that. We had a ‘Family Dinner’ each time, of course, but we were so caught up in the whirlwind that I don’t think we knew how to actually celebrate the experience as a new chapter in our lives. That’s not just something you can do without planning, and we really didn’t think about that until it was too late.” – Marty, 56, New Hampshire

5. I Wish We Would’ve Planned More Parties

“My wife and I are both big introverts. At least, we were when we met, and through most of our early relationship. After our kids were born – we have two girls and a boy – we couldn’t really avoid being social anymore. So, we decided to lean into it and throw a dinner party with some of the new friends we’d made as parents. We had a blast. We genuinely enjoyed ourselves, and the whole experience really helped our self-confidence as individuals, as a couple, and as parents. We didn’t turn into extroverts overnight, but it made us realize that making a conscious effort to step out of our comfort zones was a good thing, and something we all would’ve benefitted from much earlier.” — Caleb, 43

6. I Wish We Would’ve Planned More Strategies For Our Emotional And Mental Health

“Without getting too detailed, our family has faced a variety of mental health challenges that we weren’t prepared for. We didn’t really use what we’d learned from one challenge to the next to help better prepare us moving forward. We basically reset back to square one, and didn’t take time to realize that this could all be part of a process. To our credit, we have learned and gotten through a lot. But knowing there are mental health issues present in a family requires planning, especially if you want to support each other.” — Ed, 44, Ohio

7. I Wish We Would’ve Planned More For Today Instead of Tomorrow.

“I think that’s a more poetic way to say we wasted a lot of time doing stuff that didn’t really matter. Maybe we were looking at screens for hours at a time instead of spending time together. Or arguing over stuff that ended up not being important. Looking back to the beginnings of our family, and the decades we’ve had since, it’s hard not to regret being concerned with stuff that ultimately affected our tomorrows instead of our todays. I think I actually wish we would’ve planned more to plan less, if that makes sense. Just to be present and in the moment whenever possible, which definitely takes thought and effort.” — Micheal, 40, Pennsylvania

8. I Wish We Would’ve Planned To Have Our Family Cook More

“No one in our family really knows how to do it, including me, and that’s always bummed me out. Cooking seems like such a fun family experience, even if it’s just one person doing the cooking while everyone enjoys the meal and the time together. But we’ve always been a family of restaurant-goers and ‘taker outers’. Recently, I’ve started dabbling, but the kids are long gone, and it’s more of a hobby for myself. Growing up, my family planned meals every week, and the food was just as much fun as the company. I regret not making that experience a part of our family plan when we could.” – Ryan, 58, California

“I didn’t have true financial education until I learned it on my own. Then I set up brokerage and 529 educational savings accounts for my three children. However, I regret not preparing them sooner. As a parent, I now understand the value of these accounts in providing a solid financial foundation for my children’s future. I wish I had understood the importance of starting early and taking advantage of compounding interest to ensure that my children had a secure financial future. I learned from my past mistakes and was dedicated to empowering my children with the tools and resources they needed to succeed. I only wish I had realized the importance of these accounts sooner, but I am grateful to have had the opportunity to make a positive impact on my children’s financial future.” — Mark, 56, Idaho

10. I Wish We Would’ve Planned More Adventures

“One thing I wish I had embraced much earlier in our family’s journey is the concept of ‘Adventure Jars.’ It might sound whimsical, but it’s transformed our family dynamic in ways I couldn’t have predicted. A few years ago, feeling the monotony of routine settling in, I introduced the idea. Each family member gets their own jar where we collectively jot down ideas for spontaneous adventures or activities. These could range from a simple weekend hike to trying out a new recipe together. The twist? Every month, we randomly pick an adventure from one of the jars, and that becomes our weekend escapade. It brought an element of surprise and excitement into our lives that was missing. Not only did it break the routine, but it also created lasting memories and strengthened our family bonds. Looking back, I wish I had thought of this earlier, injecting a sense of spontaneity and shared excitement into our lives.” — Jonathan, 39, Illinois

11. I Wish We Would’ve Planned To Volunteer

“My kids have grown up to be pretty selfish. I don’t mind saying it, because I take some responsibility. They’re not bad kids, but we never really impressed upon them the importance of giving and being selfless. Which is strange, because I spent a lot of time with my family volunteering around our town, especially during the holidays. It’s one of those things you think you don’t have time for when you’re raising a family. But, looking back, I realize it’s one of those things that I should have made time for. Even planning something as simple as going to volunteer at a homeless shelter every Thanksgiving – just for the day – probably would’ve helped instill some of those values and brought us closer as a family.” — William, 50, Illinois

“How do you do that, though, right? Maybe that’s a cheat answer, but I really do believe there are ways for families to plan for unexpected events — good and bad — that our family didn’t embrace. And, really, it comes down to being supportive. Being supportive is sort of implied in a family unit. But sometimes, when things get rough, you wonder. I’m talking mostly about my wife and my relationship with our kids. We did our best to let them know they were always loved, but I think we could’ve planned our approach more effectively when looking at situations we couldn’t predict. Having a game plan, really. Even if it was something as simple as, ‘We agree to wait 24 hours before discussing anything so we can cool down and be rational.’ You really can’t just wing it if you want to create a strong foundation for your family.” — Robert, 54, Winnipeg, Manitoba, Canada



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