My Late Father's Advice That Changed My Life Forever

It is about money, but is also about far more than that, and it can help you, too

One of my very favorite pictures of me and my dad

Hi, my friend.

I start my newsletter posts like that as a small way to honor my dad. That’s how he greeted practically everyone he talked to — and believe me, he talked to most everyone who came within earshot.

Oh, my goodness, my dad could talk. He’d chat up the person behind him in the grocery store line. He’d know the waiter’s or waitress’s life story before the food was served. He’d talk trash during a game of Uno until the whole table was in tears, laughing.

Like any good dad, he gave me plenty of advice, too. Like any stubborn child, I didn’t take a lot of it. But one piece of his advice stands out more than any other. In fact, I centered an entire personal finance book around it.

“It never hurts to ask. The worst thing that can happen is that they say no, but if they say yes, amazing things can happen.”

You’ve heard that one before, right? I know my dad didn’t come up with it himself, but it speaks perfectly to what made him unique. I think of him every time I hear it or say it.

Living up to dad’s example

It also speaks to how different he and I were. We certainly had plenty of similarities — I can’t tell you how many times I’ve been told I look just like my dad, for example — but like any father and son, we were also very different. Different politics, different musical tastes, and so on. Nowhere were we more different, however, than when it came to talking to people.

My dad wasn’t afraid to ask anyone for anything at any time. Some of that confidence came from 35 years of managing people in his job at State Farm Insurance, but most of it, I believe, was just who he was. It was just easy for him.

It isn’t easy for me. Not by any stretch.

I talk for a living, but it still terrifies me to raise my hand in a room of people. I get sweaty palms when I have to tell the person behind the counter that I didn’t get what I ordered. At social events, I’m more likely to be standing against the wall, trying to drum up the courage to speak with somebody, than I am to just insert myself easily into conversation.

I’m working on it, though. Over the years, I’ve mustered up the courage to negotiate my salary, ask for fees to be waived and other things big and small — in part because I hear my dad’s voice in my head when I think about it.

Can’t hurt to ask, son. Worst thing that happens is they say no, right?

And there is no doubt whatsoever that I never would’ve gotten a book published without that voice in my head. I heard it when I asked other authors to review my proposal or introduce me to their agent or when I reached out to people for interviews. Every step of the way, the advice helped push me along.

Going through it to get over it

In many ways, writing my book was one big therapy session for me. I got to speak with more than 110 people about the good things that can happen when you’re brave enough to advocate for yourself. I spoke with therapists, authors, confidence coaches, psychologists, podcasters, journalists and others about how to power through the fear and speak up.

One of the messages that kept coming through was this: Sometimes the only way to get over it is to go through it.

Countless experts have told me that to conquer the fear, you often have to experience it. You have to feel your heart pounding, your hands trembling, your voice shaking. In doing so, you eventually feel them subside, your body telling you, It’s OK. You’ve made it through. You’ve survived.

Referring to it as survival may sound overly dramatic to some, but for many of us who struggle with these fears and anxieties, that’s very much what it can feel like. In a way, these feelings run counter to my dad’s advice. It literally can hurt to ask. A stress-induced headache is a perfect example.

However, the truth is that, in most cases, it doesn’t hurt for long. Plus, if you’re willing to put yourself out there enough, eventually it may not hurt at all.

Here’s an example…

My son, like many of us, is anxious about picking up the phone and calling people. In looking for a summer job while home from college, my wife and I had him follow up his online applications with a phone call to the business. The first few calls were nerve-wracking for him. The eighth and ninth calls, not so much. (Love these teachable moments as a parent.)

His grandpa would have been proud. He definitely would have teased his grandson a little about being so nervous, but he would’ve been super-proud.

Tips for the next time you need to speak up

• Role play. It may sound silly, but walking through a pretend conversation with a trusted friend or relative can really help. You obviously won’t be able to predict exactly how the call will go, but simply going through the motions can make you feel more confident when you actually make the ask. Be sure to do it a few times, too: Perhaps one where everything goes perfectly, a second where your friend pushes back a little bit, and then a third where the other person gives you a hard time.

• Script it out. As much as we might like to think of ourselves as being fast on our feet in negotiations, most anyone would likely be well-served by writing out at least some of what they’ll say. Even if you only think through how you’ll introduce yourself and make the initial ask, it can help. My book is filled with word-for-word scripts for how to make all kinds of asks, from a reduced credit card interest rate to a lower rate on a gym membership and more.

• Give yourself a break. You’re going to flop sometimes. You’re going to sound silly sometimes. It’s OK. Everyone has a rough day. Be kind to yourself, learn from what didn’t go so well, and keep moving forward. Beating yourself up about it doesn’t solve anything.

• Remember the last part of my dad’s advice. “If they say yes, amazing things can happen.” Don’t let the fear of getting a no kill the possibility of a yes.

Happy Father’s Day, Dad. Thank you for everything.

Love,

Matt

More Father’s Day financial wisdom

I’m honored that Chris Taylor from Reuters included me in his Father’s Day-themed newsletter post this week.

Taylor asked his followers to share the best financial advice their father had given them, and he chose a dozen to include in the newsletter.

Having just read my post, you might be able to guess what advice I shared, but there’s plenty of other wisdom in that post, so I’d highly recommend checking it out.

Kicking cancer’s butt

I’m on a mission to raise as much money as possible for cancer research in my late dad’s honor. It would mean the world to me if you’d consider contributing to my GoFundMe for the American Cancer Society. I’ve raised $6,650 to date, but I’m nowhere near done. Even a few dollars can make a difference.

Your Dad’s best advice?

Of course, I’d love to hear what your dad shared with you about money. Tell us about it in the comments below!