10 Regrets Every Parent (& Grandparent) Can Avoid

Parenting is really, really tough. It seems that as soon as you start figuring out a few things, your kids are grown. Because of this, some of the best lessons are found in what others have learned before us along the parenting journey. These lessons are usually conveyed as statements of regret. Having worked with parents of graduates for over 20 years, here are some of the biggest parenting regrets I have heard the most.


I typically hear this most right after high school graduation or about a semester into college. Especially when their children begin to struggle, parents ask what can be done to get their children to be committed to Christ and an active part of a supportive church. The problem for many is that they have spent years up until this point making other things a priority in their kid’s lives, and never made time for spiritual development or a commitment to church. I hear so many parents express regret over investing countless weekends and resources in things (ie. travel sports) at the expense of commitment to church.

If we have taught them for years that leisure activities are more important than church, why would they be convinced differently when they get to college or have their own family?

Challenge: Identify what matters most for your family. Once you have identified those values that are most important, let those things drive how you prioritize your time and resources. Talk about family values with your kids and let them in on how priorities drive decisions in your home. Make spiritual development a big deal. Make Jesus the biggest deal. Value family over stuff. Keep the main things, the main things.

Remember, YOU dictate what’s important.


This one is all about freedom and discipline. If the end goal is to prepare students for responsible independence by the time they graduate, then we have to take a measured approach to freedom and discipline. We (parents) often get this backwards. The least amount of freedom should be given when they are young (think “short leash”), but as they mature, children should be given opportunities to earn more and more freedom. As they fail, we tighten the leash and use discipline and coaching to help them learn and grow. We then give them more freedom and the opportunity to prove their responsible independence.

When parents reach out to me in crisis and let me know that their kid has failed in some area, I often catch them off guard by saying “congratulations!” While I am truly sorry they are in crisis, I want to remind them of the incredible opportunity they have to help their kids fail well. These are learning opportunities that are (hopefully) rare.

Challenge: Give your kids opportunities to fail. I promise, it’s OK. As they do, coach them through it and help them grow. Measured independence and discipline should both be very intentional. Be wise in the dangers you expose your kids to, but realize the very best time in their lives to learn lessons is when they live in such close proximity to loving parents who can help them grow and learn to make wise choices.

Remember, the goal is not raising perfect kids…but prepared kids.


Every parent will one day find themselves cleaning out a closet full of broken toys and outdated electronics. While these are all things that were given out of love because their child “needed” them, eventually both children and parents realize these were not the things they needed most from their parents. I have never had a college student tell me that they regret not having more “toys” in high school. But I have had countless tell me that they regret not spending more quality time with their family. While quantity of time is important, it is the quality of time that makes the biggest impact.

I once planned a “Family Game Night” at home as a cheap alternative to taking my kids to an expensive entertainment venue they had been asking about. When I tucked my son in bed that night, I was thinking he was probably disappointed in having to stay home and play games with mom and dad. To my surprise, he gave me the biggest hug and said, “Tonight was the best night EVER!”

Challenge: Don’t buy the lie that you serve your family best by working more hours to buy them more “stuff.” Of course parents love providing nice things for their children, but let’s not lose sight of their deepest needs. Let your calendar reflect an intentionality to capture quality time with your kids.

Remember, the greatest of presents is your presence.


I’m amazed at the number of parents who feel like they don’t even know the person they drop off at college. In a device-age, families are struggling more and more to actually connect with each other. Many are checking social media to find out what is happening with their kids. While being attune to their social media presence is certainly good, there can be a false sense of “knowing” each other based on snapshots and carefully composed taglines. Meaningful conversation takes time and cuts beyond what they do to who they are.

Challenge: Create time and space for communication in your home. There are two environments that tend to encourage meaningful conversation in the home.

#1 Dinner Table – Reclaim the dinner table as a sacred place for intentional conversation. This starts with banning devices (absurd, I know) and asking open ended questions. (“What is one good thing and one bad thing that happened today?”)
#2 Bedside – When children are babies, parents tend to spend a ton of time by their beds talking, telling stories, and praying together. Too many stop doing this as their children get older. Commit individual time with each child each night to pray, share stories, and talk about those things that matter most. Steer the conversation towards their greatest needs. (unconditional love, acceptance & value, and significance & purpose)

Remember, at their core, children want to be known. Do the hard work of making that happen.


Great teachers and coaches know that you can run a classroom or program with defined culture and set rules, but you must teach and coach students as individuals. This concept is especially true in parenting. One-size-fits-all may work for some things, but not parenting. Each child is wonderfully complex, and truly one of a kind. While there are certain needs that every child shares, each child has their own personality, temperament, learning style, giftedness, and unique needs. To lead them and grow them, you must understand and play to those differences.

Challenge: The more you know your child, the more you understand what it takes to motivate, challenge, encourage, discipline, and coach them. Don’t get lazy by failing to parent your children as individuals. Don’t get hung up on it being “unfair” to use different parenting strategies for each kid. If the goal of parenting is to best prepare your children, use those techniques and strategies that best capture their individual heart and play to their unique originality.

Remember, one size does not fit all in parenting.


It’s a shame that our kids do not realize just how cool we actually are. Because they (especially teens) struggle to see this, some parents go to great lengths to prove this to them. The temptation in this is to take on the role of their friend, and abandon the role of a parent. While your kids will have opportunity to have a lot of friends, they only have one opportunity to experience what you uniquely offer them as a parent.

Challenge: Parent them while you still have that opportunity. When your children are grown, you will have a chance to be their friend. Use this limited time in their lives to lead, love, correct, coach, and disciple…as a parent. Embrace your unique role in your child’s life. Don’t surrender the blessing of parenthood for a lesser role.

Remember, the most significant role you can have in your child’s life is PARENT.


Peer pressure is real in parenting, especially when coupled with the constant overture from your kids “but every other parent is doing it!” When faced with difficult decisions, it is certainly easy to look around and survey popular opinion. While a “go with the flow” approach to parenting may be easier in the moment, it certainly does not give you the best long term returns.

Challenge: You are accountable for what God has entrusted to you. When faced with difficult parenting decisions, do the work of praying through the decision, searching biblical wisdom, and seeking Godly wisdom from trusted sources. Ultimately, you must parent based on what is best for your child and what supports your parenting aim.

Remember, Godly counsel is infinitely more reliable than popular opinion.


Sometimes being a parent feels like you’re a scheduler, an Uber driver, an air traffic controller and a personal shopper all in one. There are days where the objective may just be to manage the chaos, get everyone where they need to be, not kill anybody, and let’s just move on to another week! Have you ever just wanted to fast forward through a day, week, season, or school grade? These feelings can be especially common when we (parents) allow ourselves to get in a managerial mindset.

Challenge: Don’t let the craziness of life rob you of the blessing and opportunities of parenting. This is all about perspective. We can either grip the steering wheel and grit our teeth as we drive to ONE MORE practice or event in rush hour traffic, or we can see that 30 minutes in the car as an opportunity to invest in our kids. We can turn the radio up and sing our guts out, roll down the windows (although not while singing, or our kids will hide), or talk to them about what their sport is teaching them. Those times of managing that crazy schedule can actually be some of the most valuable teaching moments and times of discipleship your family will ever have. We are parents, teachers, and spiritual leaders. Let’s redeem every opportunity to lead.

Remember, everything on your schedule provides an opportunity to lead.


I see so many students who go off to college and spiritually crash the first time Professor Wine & Cheese challenges their faith. When they are told that their faith is a crutch, their parents are wrong, and that Christianity is for those who are weak-minded, so many students don’t even know how to respond. The absolute best thing we can do for our children is to help them own their faith in Christ. This involves not only leading them to know truth, but helping them understand why it is true.

Challenge: Put in the work to help your children know what they believe, and why they believe it.  Help them discover, and allow them to question. Don’t freak out if they have doubts or ask tough questions. Now is the best possible time for them to explore their faith and “work out” what is true. So many parents don’t encourage this because they fear their kids may ask them questions they don’t know the answer to. One of the most powerful things you can say to your child is “I don’t know, but it is important enough to me that I will help you find the answer.” The most important legacy you can give your child is well tested truth. How are you helping them own their faith?

Remember, your children cannot live off of your faith.


We have a plan for a lot of things in our homes… a financial plan, a retirement plan, a meal plan, a plan for extra-curricular activities. All of these plans are important because we know that “If we fail to plan, we plan to fail.” But what about a parenting plan? Do we have an actual plan for how we are going to avoid the types of regrets mentioned above, or do we plan to make it up as we go?

Having a plan is so important, it is a HUGE part of what I do in ministry to students and families through our Grounded for Life spiritual growth plan. In fact, before students graduate from Student Ministries, we lead each student through a process of writing an ACTUAL PLAN of how they are going to experience God’s best for their lives beyond graduation by living out the truth of God’s Word. (For more info on Grounded for Life, click here.) Putting a plan on paper has proven to be so much more effective than simply graduating with good intentions.

Challenge: Don’t overcomplicate this, and don’t put this off. Write down those things that matter most to you as a parent. Use these statements of regret from other parents as a guide to create intentionality in each of these areas. Once you’ve identified those things that matter most, tweak your schedule, budget, and boundaries for your home to reflect what you really want for your family. Share these things with your kids and share them with friends and family who can offer you encouragement in these areas. As you invest time in this, be encouraged that you are doing work that will shape the lives and futures of your kids, and grandkids.

Remember, most parents do not plan to have regrets; they just don’t plan NOT to.


This is an important reminder for grandparents as well. One of the blessings of being a grandparent is you get a “do-over” of sorts with those regrets you may hold on to from parenting. You get to take all the lessons you learned as a parent and pass them on to your children as they navigate the same unknowns, fears, and trials of parenting their kids.

You get to have a unique and powerful voice in the lives of your grandchildren. Embrace your special role as a grandparent, and continue your ministry of building a legacy of faith that will impact generations to come.

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