After raising five beautiful children of my own and supporting hundreds of families through my 20+ years as a midwife, I’ve heard countless parents reflect on their journey with those bittersweet words: “If I could do it all over again…” Today, I’m sharing those valuable parenting do-overs that experienced mothers and fathers wish they’d known from the start—insights that might just make your own parenting journey a little smoother.
The Wisdom That Comes With Experience
My oldest just graduated college, while my youngest is navigating middle school. This perspective—spanning diapers to diplomas—has shown me that parenting wisdom often arrives precisely when we no longer need it for our current stage! When my first baby wouldn’t sleep unless held upright on my chest, I was convinced I’d never sleep again. By baby number five, I knew that these phases pass in the blink of an eye, even when the nights feel eternal.
The beauty of learning from experienced parents is that their parenting do-overs reflect real-world testing—not theories or idealized scenarios. These insights come from the trenches of sleepless nights, toddler tantrums, teenage negotiations, and everything in between.
According to a national survey by Pew Research Center, nearly 62% of experienced parents say they would approach certain aspects of child-rearing differently if given another chance. Let’s explore the most common reflections I’ve gathered from both my personal experience and the hundreds of families I’ve supported through my midwifery practice.
The Paradox of Parenting Experience
One mother in my prenatal group captured it perfectly when she said, “By the time I figured out each stage, my child had already moved on to the next one!” This sentiment echoes across playgroups, school pickup lines, and my midwifery practice.
Parenting often feels like assembling furniture without instructions—just as you figure it out, you realize you’re building something entirely different than what you started with. These parenting do-overs acknowledge that reality while offering guideposts for those still in the midst of their journey.
What Experienced Parents Would Do Differently: The Early Years
Worrying Less About Developmental Milestones
If I had a dollar for every parent who told me they’d stress less about milestones the second time around, I could retire early! First-time parents often track each roll, crawl, and step with vigilance that can overshadow the joy of simply witnessing their child’s unique development pattern.
Maria, a mother of three who attended my parenting support group, shared: “With my first, I literally lost sleep when she wasn’t walking at 12 months like my neighbor’s baby. With my third, I celebrated the extra months of her not being mobile as a gift! She walked at 15 months and is now a college athlete. All that worry for nothing.”
What experienced parents recommend instead:
- Understand the wide range of “normal” development
- Focus on your individual child, not comparisons
- Communicate concerns with healthcare providers rather than Google
- Remember that development isn’t linear or competitive
During my years as a midwife, I’ve seen how the pressure around milestones can rob parents of present-moment joy. Among common parenting do-overs, releasing milestone anxiety ranks near the top.
Being Less Rigid About Sleep Training and Feeding Methods
Oh, how many dogmatic stances on sleep and feeding I held with my firstborn! I was convinced that one particular method was the “right” way until my second child promptly proved that theory completely irrelevant to her personality.
John, a father of four who participated in our fathers’ support program, reflected: “I wish I hadn’t been so hard-line about sleep training with our oldest. We followed this strict method that worked, but at what emotional cost? With our younger kids, we found a middle ground approach that respected their needs while still teaching them to sleep independently.”
What experienced parents recommend instead:
- Recognize that different children respond to different approaches
- Be willing to adapt methods to fit your child’s temperament
- Trust your intuition alongside expert advice
- Remember that responsive parenting matters more than strict adherence to any method
The most successful families I’ve supported through my two decades as a midwife approach parenting methodologies as tools in a toolbox rather than biblical commandments.
Taking More Photos and Videos of Everyday Moments
This parenting do-over comes with a twist—most experienced parents wish for fewer posed holiday photos and more candid captures of ordinary days.
Rebecca, mother of teenagers, shared tearfully at a school event: “I have dozens of Christmas card-worthy photos but missed recording his little voice singing in the bathtub or the way she used to mispronounce ‘spaghetti.’ Those ordinary moments are what I’m most nostalgic for now.”
What experienced parents recommend:
- Capture the mundane moments—messy faces, bedtime stories, backyard play
- Record their voices and mannerisms at different ages
- Take photos that include you with your children (not just of them)
- Create simple systems to organize digital memories before they overwhelm you
As both a midwife and mother, I encourage parents to document their journey authentically—the beautiful chaos of everyday life contains the memories you’ll treasure most deeply.
Mid-Childhood Parenting Do-Overs
Setting Boundaries Earlier and More Consistently
Among the most common parenting do-overs I hear from experienced parents of school-aged children involves establishing clear boundaries from the start.
Michael, father of three now-teenagers, shared during a parenting workshop: “We wanted to be the ‘cool parents’ who rarely said no. By elementary school, we were exhausted from negotiating everything from bedtime to screen time. Starting over, I’d establish loving but clear boundaries from day one.”
The research backs this up. According to the American Academy of Pediatrics, consistent boundaries actually help children feel more secure and develop better self-regulation skills.
What experienced parents recommend:
- Establish family values and boundaries early
- Be consistent across caregivers when possible
- Focus on the “why” behind rules so children understand their purpose
- Remember that boundaries are an act of love, not restriction
In my midwifery practice, I often remind new parents that setting loving limits is preparing their children for a world that won’t always cater to their every desire.
Making More One-on-One Time With Each Child
With my first three children spaced just four years apart, individual attention often got lost in the beautiful chaos. This remains one of my own greatest parenting do-overs—wishing I’d been more intentional about one-on-one connection.
Sophia, mother of four grown children, reflected during a grandparenting preparation class: “Looking back, the most meaningful memories my adult children share aren’t the elaborate vacations or expensive gifts—they’re the simple times when they had me or their father all to themselves, even just for an hour.”
What experienced parents recommend:
- Schedule regular “dates” with each child, even if brief
- Create bedtime routines that include individual connection
- Find activities that celebrate each child’s unique interests
- Be fully present during these times (phones away!)
The quality of attention matters far more than the quantity. Some of my most treasured parenting memories came from simple car rides alone with one child or bedtime chats that extended just a few minutes longer than usual.
Worrying Less About Academic Achievement
The academic pressure cooker starts shockingly early in today’s world. Many experienced parents cite academic obsession as a significant parenting do-over.
James, father of college-aged children, shared: “We were so focused on reading milestones and math enrichment that we sometimes missed seeing our children’s actual passions. My son who struggled with reading is now a successful architect who designs buildings—his spatial skills were always his strength, but we were too focused on getting him to grade level in reading to notice.”
What experienced parents recommend:
- Focus on cultivating curiosity and love of learning over grades
- Recognize and nurture your child’s unique intelligences
- Remember that developmental timelines vary enormously
- Support academic growth without making it the center of your relationship
As a midwife who has followed families from birth through young adulthood, I’ve seen that emotional intelligence and resilience often predict success more accurately than early academic achievements.
Teenage Years and Beyond: The Long-View Perspective
Building Independence Earlier
Perhaps the most bittersweet parenting do-over involves preparing children for eventual independence—a process many parents wish they’d started earlier.
Elena, mother of three adult children, reflected: “I did too much for them for too long. I thought I was being a good mother by handling everything, but I now see I was actually making them dependent on me. I should have been teaching them life skills all along.”
What experienced parents recommend:
- Assign age-appropriate responsibilities from early childhood
- Teach practical life skills gradually and consistently
- Allow natural consequences when safe to do so
- Remember that independence builds confidence
In my parenting workshops, I often remind participants that our job isn’t raising children—it’s raising future adults. This perspective shift helps frame independence as the goal rather than a rejection of parental care.
Focusing More on Character Than Achievement
When asked about their greatest parenting do-overs, parents of adult children overwhelmingly mention wishing they’d emphasized character development over achievements and accolades.
Thomas, father of grown daughters, shared during a grandparenting class: “I was so proud when my daughter made the honor roll, but now I’m most proud watching her show integrity and compassion as an adult. I wish I’d celebrated those character moments as loudly as I celebrated her academic ones.”
What experienced parents recommend:
- Explicitly name and celebrate acts of kindness, courage, and integrity
- Create family values that emphasize character qualities
- Model the character traits you hope to see in your children
- Remember that who they are matters more than what they achieve
As both a midwife and mother, I’ve observed that children absorb our priorities through what we celebrate and discuss most frequently. When we consistently highlight character, it shapes their understanding of true success.
Making Self-Care a Priority, Not an Afterthought
Perhaps the most frequently cited parenting do-over among the parents I’ve supported through my midwifery practice is neglecting their own wellbeing while raising children.
Amara, mother of teenagers, reflected: “For years, I believed being a good mother meant putting myself last in every situation. I now realize my constant exhaustion and resentment weren’t helping anyone. When I finally prioritized sleep, exercise, and occasional alone time, I became a more patient, present parent.”
What experienced parents recommend:
- Recognize that self-care enables better parenting
- Start small with sustainable self-care practices
- Model healthy boundaries for your children
- Build a support network rather than attempting to do everything alone
I often tell new parents in my practice that self-care isn’t selfish—it’s actually deeply selfless because it ensures you have the resources to parent from your best self, not your depleted self.
Universal Parenting Truths: What No One Regrets
While parenting do-overs vary widely based on individual circumstances, certain choices remained regret-free across nearly all experienced parents I’ve encountered:
- No one regrets extra cuddles, bedtime stories, or lullabies
- No one regrets choosing connection over convenience in challenging moments
- No one regrets apologizing to their children after parental mistakes
- No one regrets creating simple family traditions that build belonging
- No one regrets putting down their phone to be fully present
During a particularly moving moment in a parenting group, a father of adult children shared: “The days were long but the years were short—exactly like everyone told me and exactly like I couldn’t understand until it was over.”
Final Thoughts: Grace in the Journey
If there’s one thread connecting all these parenting do-overs, it’s the need for grace—both for ourselves and our children. Perfect parenting isn’t just impossible; it wouldn’t even be good for our children, who need to see us navigate imperfection with resilience and humility.
After five children and supporting countless families through birth and beyond, I can say with certainty that love overshadows our mistakes. Children are remarkably resilient when raised in an environment of consistent care, even when that care isn’t perfectly executed.
So take these lessons from experienced parents not as another standard to measure yourself against, but as gentle guidance from those who’ve walked before you. Integrate what resonates, leave what doesn’t, and remember that you’re writing your own unique parenting story—one that will contain both mistakes and moments of breathtaking beauty.
The greatest gift we can offer the next generation of parents isn’t a blueprint for perfection but permission to learn as they go, just as we did. After all, the most powerful parenting do-over isn’t about the past at all—it’s about how we choose to show up today, tomorrow, and all the days we’re fortunate enough to guide these remarkable little humans toward adulthood.
