The Moneyist: I Earned $5 Million In My Lifetime—now My Long-lost Son Keeps Hitting Me Up For Money

Dear Moneyist,

Everyone is pressuring me for money. My success has caused strife, greed from others and sadness for me at every turn. I have been fortunate to become a successful small business owner. My assets exceed over $5 million. One would never know it due to my non-flashy lifestyle (used cars, modest home, etc.).

I fathered a child after one date in my teens. The mother was from out of state. I tried to be responsible and provide what I could at that time. Two years after he was born, I was asked to not contact the mother anymore. She was getting married to someone that would accept my son as his own. Since I was only 19 and she lived across the country, I didn’t fight it.

For many years, I always wondered how he was doing and carried guilt. I searched for him over the years, but couldn’t find him. I even stashed U.S. savings bonds for him before my success, thinking that I could help him with college.

Fast forward to 2012, my son’s mother was getting a divorce and she found me. I not only discovered my son, but discovered I was a grandfather to a 9-year-old girl!

I arranged to meet them in their state. I had a wonderful time, and paid for everything including my son’s mother and her extended family. I never mentioned my financial situation and kept that low key. (As I always do.)

Don’t miss: I love my girlfriend, but she spends all her money on vacations and clothes

Shortly after meeting them, my son and his wife came to visit me. Somehow, he discovered I had resources. That’s when the requests for help started. He always seemed to have problems with his car, paying his rent and maintaining a job.

Within a little less than a year, I had probably spent $10,000 on lots of little emergencies. My son would ask for money as a loan, but always had a worse situation come up needing more with an excuse for not paying me back.

I also have two brothers that are not doing well financially and an elderly mother living on a fixed income. All of them, including my mother, are always asking for me to help them with needs.

Also see: My new wife wanted to live with me for free, even though she had $800,000 in the bank—so I asked her to move out

My wealth was not handed to me. I worked hard and have pinched pennies all my life. I don’t wear designer clothes, go out to eat regularly and I never needed to have the newest iPhone.

Everyone else is the opposite. They drive cars they can’t afford and make financial decisions I would never dream of. Every time I help someone in my family, someone else feels they have been left out.

I recently stopped helping all of them, except for my mother. I reduced my generosity with her to just covering her needs. You would think I was the most awful person in the world. (I should say, I am made to feel like I am awful).

The comments are hurtful. They say that I am selfish, lucky and I don’t need the money I have. It is relentless. Even the mother of my child, who I have only seen once in 33 years, called me asking for $20,000 to start her own business.

She told me what an awful person I was because I was not around to care for my son. My brothers say I don’t care about them or my own mother even though I pay her rent and expenses. I reduced my mom’s money because my brothers still ask her for money!

What can I do or say to let everyone in my life understand that I love them, but I am not an ATM machine? I wonder if things would have been the same if I had spent my money on myself instead of always helping everyone else?

I am so frustrated. I have a notion to reflect my feelings in my estate.

Father/Brother/Son in Missouri

Dear Father/Brother/Son,

It’s hard to make up for all that lost time with your son. His mother decided to move and start a new life with another man and wanted you out of the picture. You reluctantly agreed and, when they came back into your life, they realized you had a lot of money.

Would it have turned out differently had you been in your son’s life? Would he have learned the lessons that you have so successfully applied to your own life? Perhaps. But paying his bills won’t rectify that now. Nor will it help him in the long-term.

You could do one thing to bridge that gap between the past and the present. Tell your son that the best way to get increase his prospects is to learn new skills and improve his education. You could offer to pay for him to attend college part-time.

But tell him what you told me: Being hit up for money on a regular basis hurts rather than helps your relationship, and doesn’t solve long-term problems. You can’t undo the past. Nor can you spend the rest of your life writing checks to make up for it.

Recommended: I asked my son to buy a condo unit with me as an investment — now I want my money

You may also want to set up an education trust or 529 savings plan for your grandchild’s education, and inform your son and his mother of your plans. There are three things you need in life to give you a head start: education, education and education.

If your son wants a relationship and wants to make positive life choices, then you can support him. I agree that he is now an adult and it’s not your role to pay for his bills. I don’t believe you should be guilted into handing out money, especially to your former girlfriend.

Also see: My father wants me to co-sign on a $300,000 mortgage — what should I do?

Perhaps there’s a silver lining to the boundaries you have set with your family. From your letter, you appear to be a single man without any children. There may be an opportunity to set up a charitable foundation or become involved with other causes that are close to your heart.

At this point in your life you should be (a) enjoying the freedom your money brings and (b) helping others who are less fortunate than you, which may include a supportive and loving family rather than people who say you owe them. Helping others may also involve giving your time.

You can be proactive about pursuing a healthy relationship with boundaries. Would you be prepared to help your son with certain milestones, such as a down payment for a home? Would your son and his mother want to be in your life if they didn’t know you had money?

No one enjoys feeling used. Would you really say that this kind of transactional relationship means they are in your life? All things being equal, what kind of relationship do you actually want with your son? And what would have to happen for you to have a real relationship?

While you navigate these questions, seek help from a financial adviser or trusted friend and, given all of these recent events, there has never been a better time to make a will.

Do you have questions about inheritance, tipping, weddings, family feuds, friends or any tricky issues relating to manners and money? Send them to MarketWatch’s Moneyist and please include the state where you live (no full names will be used).

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