All Things Financial Planning Blog

A Letter to My College Bound Son


Dear Colin,

In a few days, you’ll pack the car and leave home to begin your college career. I can’t deny the big lump in my throat as I say this and imagine your empty seat at the family dinner table and your eerily quiet and tidy bedroom. I will miss you, terribly… how your wacky humor makes me laugh, how your unique perspectives on life make me think, and how even in your crankiest moods, you flash those intense blue eyes, full of passionate beliefs and determination that show the promise of a man who will make a difference in this world.

From the moment you were born, I knew the day would come when it’d be time for you to go. That “someday” is now. You’ve grown strong and capable. Like a bird, you’ve outgrown the nest and are ready to fly. 

You’ve been preparing for your “independence day” for some time. You’ve practiced managing your personal life, school, work, and money. Through trial and error, successes and mistakes, you’re figuring out what works for you. 

Healthy money behaviors have come naturally to you. You do a good job balancing spending to enjoy today and saving for the future, being a smart shopper, and avoiding debt. You are willing to work for what you need and want. Remember those 5am alarm bells and how hard you worked in the warehouse this summer? Easy money? No way! I know you’ll spend your money with care and make it last through the coming school years.

Reaching agreement about what to expect from each other is one of the most important ways we have prepared for this life transition. Putting things in writing is sometimes more powerful than speaking the words. So here it is. Let’s both promise to keep our word.

What you can expect from us:

  • Our love and moral support.
  • Financial support in the ways we have discussed.
  • Respect.
  • Room to grow – no helicopter parenting.
  • Won’t change your bedroom (at least for now).

What we can expect from you:

  • Your Job:
    • Value and appreciate this investment in your personal growth and your future.
    • Attend all classes, do the work to your best ability and on time.
    • Be engaged and get involved on campus.
    • Handle things on your own; get help immediately when you can’t.
  • Your Money:
    • Give yourself a weekly allowance and stick to it. 
    • Pay with cash or debit card.
    • Use your credit card for emergencies in the ways we have discussed.
    • Check your bank account online at least once a week.
    • Monitor automatic banking text and email alerts.
    • Don’t lend or borrow money from friends. 
    • Protect your valuables – most of all, your identity.
    • If you lose or break something, replace it at your own expense.
  • Your health:
    • Eat healthy, get enough sleep, and exercise.
    • See a doctor when you must.
  • Communication:
    • Check in at home once a week – email, text, phone, I-Chat.  (More is okay too.) 

Aside from our agreement, I also want to share my highest hopes as you take this big step towards creating your own future. Thanks for listening just a minute longer…

Own it.
It’s your life and you’re in charge. How to spend your time, talents, energy and money is up to you. Do it with purpose. When in doubt about what to do, ask yourself: How does this impact my life? How will it make my life better? Will I be happy with this decision later? Can I live with the consequences if I make a bad call? Remember that independence comes with rewards and responsibilities.

Be your own person. 
Be true to who you are. I know you’ve heard this a million times. Sure, it’s good to appreciate differences and diversity, as long as you don’t get caught up in other people and lose yourself. Continue to be your own man. You’ll respect yourself and others will too. Remember that you cannot buy happiness, and that money has nothing to do with the value of a person. There will always be people who have more and less than you. Comparing and trying to keep up with others is a waste.  Manage your money and your life on your own terms.

Dare to do great things. 
Your childhood hero, “Woody”, from the movie Toy Story, said it best,”Reach for the sky!” This is your time to discover all you are capable of becoming and contributing to the world. Now, more than ever, believe in yourself and explore your passions. If you do, success will come—in the ways that you will choose to define a successful life. At the same time, expect challenges. Life is difficult! Have confidence that when you struggle, you’ll be stronger and smarter than if you succeeded on the first try. To get through life’s inevitable challenges, trust yourself and the support of your safety nets, including those who love and care about you— most of all, your family. 

Your Dad, Nate, Ryan, Toby and I love you, Colin. Let our love give you roots and help you find your wings. Fly!


karinMaloneyStiflerKarin Maloney Stifler, CFP®
True Wealth Advisors
Hudson, OH

Author: Karin Maloney Stifler, CFP®, AIF®

Karin Maloney Stifler, CFP®, AIF®, has practiced as a Fee-Only TM Certified Financial Planner® professional for over 18 years with nationally recognized firms in Boston, Chicago and her native Cleveland. She founded True Wealth Advisors based on her belief that fiduciary financial planning can benefit people from all walks of life, at all stages of life. She is honored to serve as a National Board member of the Financial Planning Association (FPA), where she led efforts to institute FPA’s national pro bono commitment after 9/11. Karin holds a BA in International Studies and MBA in Finance. Personally, Karin enjoys yoga and running in her quest for health, balance and energy to keep up with three growing sons.

29 thoughts on “A Letter to My College Bound Son

  1. Karin, this is beautiful! I’m reading this in a hotel room the night before we move our son back in for college year #2. This is just as valuable this year as the first year, maybe more so with the perspective of a year already completed for both son and parents – and lessons learned! Thanks for sharing this.

    • Hi Shelley,
      Thanks for your comments. I hope that you and your son are doing great and are poised for a terrific year ahead. Take care!

  2. Karin–this is both beautiful sentment and ver practical info. I am going to pass it along to friends now and save it for my daughters in the (not too distant) future. Thanks for sharing.🙂

  3. Ah Karin! What a lovely letter. I feel like we’ve prepared our children so well for college academically, but maybe not so well in other ways. Thank you for the article. There are so many useful thoughts and ideas packed into a few paragraphs! I’m showing it to my daughter right now. . .

  4. Karin,

    How do I clone you? If every parent prepared his or her child for college like this, the world would be a much better place! Bravo.

    • Hi Susan,
      Your comments are very appreciated, especially since you are the expert on the topic of helping kids to become independent, decent and productive citizens. “It takes a village”, as they say, and I’m grateful to have many special people in our village – you included! Be well~

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  6. My daughter is only 4 months old, but I printed this letter and I hope I can dig it up when she’s a little older — excellent advice. Thanks for sharing this.

  7. Wow, I appreciate my own mom so much more after reading this annoying rant.

    Love you mom!

  8. I read your blog about the Letter to my son through a link in the financial blog of New York Times. No one couldn’t have said it better than you. My son is bound for Kindergarten next week and I hope that I can instill some advice into him when he is challenged in life and has to make a decision. Thanks for the wonderful write up.

  9. Wonderful thought provoking emotional letter. I have come to drop my 2nd daughter to the US all the way from India. I will go back to an empty nest now. My wife is already experiencing it and the feeling is overwhelming. Your writing struck a chord and I forwarded that to my daughters. Thanks for sharing your feelings with us. It reflects what many parents are feeling right now in some corner of the world.

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  12. Karin, Thank you for sharing. I am 42, I have a 21 son, 19 and 16 yr olds, and I am also a grandparent of a 1 yr. As I was reading your letter…. I felt as if you were talking to me, I wish it were coming from my mother. But as a young mom and raised my kids alone, I enjoyed your write up for both my children and myself. Lots of lessons life gives you and plenty you learn on your own through many ooops, without support or guidanance. As a mom, grandmother and a person that its still learning to grow I do appreciate wisdom from others. This is the first time I comment on line and I would like you to know that just as well as your son this letter will bwe read and reread over again. Thank you for sharing your inspireration. I wish you and your family the very best.

  13. Karin,
    This is beautiful! And thought provoking, and applicable to all parents who want to teach their children to be good stewards.

  14. Pingback: Back to School: A Mother’s Financial Advice For Her Son | Ally Straight Talk

  15. Hi Karin!

    I am an English student who tries to write an advice letter as homework. I was searching on the internet for some information about it and I´ve found your beautiful letter!!


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