Dear Ruby,
I would like your opinion on something.
I few weeks ago I listed a small boat on FB. The boat has been sitting in my driveway for several years with the intention of teaching my grandchildren to sail. I even bought spare and replacement parts in preparation.
I got numerous requests for more pictures and requests for its condition to which I responded promptly. Many said they wanted to see it but when it came time to meet there were excuses and delays.
Finally, a mother called and said her son wanted to buy it to learn to sail. He had saved his money and he was ready to make the purchase. At that point I was so happy to find out a teen wanted to learn, I said he could have it for free and I would even deliver it.
His dad called and insisted he that he pay for at least part of the price as a life lesson, and I agreed. The day came, I delivered the boat. No one was there to receive it, and I felt relieved that I didn’t have to go through the awkward moment of taking his money. I sent a message that I needed to leave and not to worry about the money. He was insisting I take something so I said worst case he could Zelle it to me.
In a subsequent message I said I am sure you are an excellent dad and to make this a lesson in receiving a gift gracefully.
I am a concerned that I was a little curt about the lesson, not to mention that I am concerned about the boat meeting his needs.
I want your opinion on the lessons. I never forced my kids to save for a big purchase, although I know they did so on their own. Even in high school when it came to cars, I told them their job was to get good marks not work after school to pay for a car.
My question is this— is “dad” setting a role example (dad being willing to support his needs) more important than a somewhat ridged lesson about money?
I might add that I have been very lucky to have three successful men, a civil engineer, a medical doctor and an architect.
Sincerely,
~Still learning
Dear Still Learning,
First, let me say how much I enjoyed reading your letter. It isn’t really about a boat. It’s about generosity, parenting, pride, gratitude, and the values we hope to pass on to the next generation. Those are conversations worth having.
The first thing that stood out to me was your joy when you discovered a young person wanted to learn to sail. Your excitement wasn’t about selling the boat, it was about giving the opportunity. That changes everything.
The father’s response also came from a good place. He wasn’t trying to reject your generosity. He was trying to teach his son that things of value come with sacrifice, responsibility, and gratitude. Those are admirable lessons, and many parents would have done exactly the same thing.
Where I think the conversation becomes interesting is this: What lesson will the boy remember twenty years from now? Will he remember paying for the boat? Or will he remember the stranger who believed in him enough to give him a chance? Those aren’t competing lessons, they’re complementary ones.
Receiving a gift gracefully is every bit as important as earning something through hard work. Learning to say, “Thank you. I will take good care of this,” is a life skill. So is recognizing generosity without feeling obligated to erase it.
Your comment about “receiving a gift gracefully” may have sounded a little direct to you afterward, but I don’t think it was harsh. I think it reflected what you were hoping the father would understand, that sometimes allowing someone to give is itself a gift. Generosity needs a willing receiver just as much as it needs a willing giver.
As for parenting, I don’t believe there is one correct philosophy. Some parents teach independence by asking their children to earn everything they receive. Others teach confidence by making sure their children know they have unwavering support while still expecting responsibility. Both approaches can raise successful, compassionate adults if they’re rooted in love rather than fear.
The evidence is sitting in your own family. You didn’t require your children to finance every milestone, yet they became a civil engineer, a physician, and an architect. That doesn’t prove your way is the only way, but it does prove there are many paths to raising capable, responsible adults.
Sometimes the greatest lesson a parent teaches isn’t, “Nothing is free.” Sometimes it’s, “When someone is kind to you, accept it with gratitude and when you are able, pass that kindness on to someone else.” To me, that may be the most valuable lesson of all.
One final thought. You worried whether the boat would meet the boy’s needs. I suspect you’re asking the wrong question. You gave him more than a sailboat. You gave him a story he’ll probably tell for the rest of his life. Years from now, he may not remember every detail about that little boat. But I’ll bet he remembers the man who believed in a young sailor enough to help him get started.
And perhaps one day, when another young person dreams of sailing, he’ll do exactly what you did. That is how generosity travels through generations.
Warmly,
Ruby