Best Mom Advice: 10 Life and Business Lessons from Mom


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With Mother’s Day coming up, I wanted to share some of the best advice and lessons I got from mom growing up. Most of the time, this was pretty literal advice, but I found a lot of it has a broader application to entrepreneurship.

Mom has always been probably my biggest advocate and supporter. For background, she essentially had a couple different careers, first in nursing and then as a library assistant.

(At the library, she actually helped me get one of my first jobs in high school.)

Lots of wisdom I hope to be able to pass along to our little ones!

And if you like this format, be sure to check out the companion list/episode on dad’s advice!

1. Keep Reading and Keep Writing

My brother (Chris at BecomingBetter.org) and I definitely watched our fair share of TV and played our fair share of video games, but reading for pleasure was always encouraged and expected.

And what I found was that by reading and taking in different styles and perspectives, I became more creative myself.

We had a stack of construction paper and crayons and markers in the desk in the kitchen that we’d turn into all sorts of projects. When I said I didn’t like the new Sonics logo, mom said, “OK, make a better one.”

I think writing is probably one of the most underrated skills in the world today, because so much of our communication happens over email or over websites.

But it’s a skill that takes practice. And I’m really grateful that mom encouraged Chris and I to keep writing.

2. “If you’re not in it, it’s just a postcard.”

Yes, I’m old enough that my first camera had real film … the kind you had to take to a store to get developed.

And upon developing one of those rolls of film, mom told me: “If you’re not in it, it’s just a postcard.”

I don’t remember what the picture was of, but apparently I wasn’t in it! That’s stuck with me both on the literal level and the metaphorical level.

If you’re ever fortunate enough to find yourself at The Great Wall or Angkor Wat or the Eiffel Tower, know that thousands of professional photographers have been there before you, in just the right light, with just the right equipment, and gotten a better shot than you could ever realistically hope to achieve.

But they didn’t have you. Get in the picture.

In all my projects, the ones that have had the most success are the ones I signed my name to, instead of trying to stay semi-anonymous, behind-the-scenes. In any business, you bring your unique perspectives, personality, strengths, and style, which can be a competitive advantage.

3. Be able to follow the instructions, but doing it your own way is allowed too.

This is a Lego-building lesson. It’s an important skill to be able to follow the instructions and pay attention to all the details.

And in business, you should absolutely take full advantage of all the case studies and mentorship of those who’ve gone before you. Why reinvent the wheel?

But “free-building” is fun too. And in business, there’s not always going to be a step-by-step recipe to follow.

4. Send Your Thank You Notes

When we’d get birthday money as kids, we were never allowed to cash those checks or spend any of the money until our thank you notes were written.

This was a small way to instill a gratitude practice, even if it felt like a chore at the time. It’s something that has stuck with me as I’ve been gratitude journaling off and on for the last decade.

5. Curation is Creation

When Chris got really into Billy Joel, Mom made him a “greatest hits” mix-tape. That illustrated the value in curation, which is still alive and well today.

Chris puts that into practice in articles of his like the essentials of Stoicism.

In online business, you see it in email newsletters, and even podcasts like The Side Hustle Show. For example, I’ve created my own “greatest hits” playlist (and others based on specific sub-topics):

Greatest Hits: Best of The Side Hustle Show

If you're not sure where to start, here are some of the most popular, powerful, and profit-inspiring episodes.

Add to Spotify

6. Do the Easy Part First

Mom is a jigsaw puzzle master, and it can be overwhelming looking at 500-1000+ randomly assorted pieces. Her advice? Start with the outline or other easy parts.

That way, you build some positive momentum, feel like you’re making progress, and are motivated to keep going.

I apply the same strategy to a lot of my writing today. Instead of starting with a blinking cursor and trying to write an introduction, I’ll outline the article and start filling in the gaps.

I find that I’m able to create content much faster that way than attempting to write it top-to-bottom.

7. An Ounce of Prevention is Worth a Pound of Cure

Brushing and flossing is cheaper and easier than filling cavities!

In online business, you see lots of examples of an “ounce of prevention” in practice. For instance, FAQ pages, products with detailed pictures and sizing information, and even advertising copy that says specifically who the product is a best fit for. All of these are designed to prevent the more expense “cure” of customer support staff, processing returns, or working with a client who’s not well-aligned with what you have to offer.

8. “Is That REALLY What You Want to Spend Your Money On?”

The first thing I remember saving money to buy was a skateboard. When I finally had enough, standing in the aisle at Toys ‘R Us, mom hit me with: “OK, is that really what you want to spend your money on?”

And if she thought it was a dumb idea — which she probably did — I don’t think that was detected by me. Instead what came across was, “Yes, you can get this. You understand how much it costs, and is that worth it to you?”

And that time it was, but on countless other occasions the answer was no, I’d rather save for something else.

A lifetime of frugality ensued!

9. Have High Expectations for Yourself

In middle school, I remember some friends of mine getting paid for their report cards. $20 for each A, $10 for each B, like that.

I can’t tell you how fast that proposal was shot down when I floated it by mom and dad!

“Why reward what’s expected?” I think was the reaction. Do your best because of who you are and care about the effort you put into the world, not because you think you’ll get paid for it.

10. “I Hope You Dance”

This was mom’s advice upon high school graduation, based on the lyrics of a song by Lee Ann Womack that was popular at that time.

It’s a call to be grateful for what you’ve got, to keep growing, to have the strength to get through the challenges ahead, and have some fun along the way. I probably didn’t fully appreciate or understand that at 18, or even 28, but definitely do know after having kids of my own.

Love you, mom!

Hopefully lots of years of dancing ahead.

Your Turn

What’s the best advice your mom gave you?

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