What I Learned About Business From My Single Mom & Entrepreneur Dad

My parents have had very different careers. But I've learned valuable lessons from them both in terms of how I approach work, business, and entrepreneurship.

an apple tree representing entrepreneurial business learning

13 min. read

I’ve written before about how growing up I never really imagined I’d end up working in business. But with a 15+ year career in marketing/communications which includes owning a small side hustle for the past five years, running a freelance practice for six years, and now working here at Proposify, it’s a good thing I didn’t have my heart set on a career in fortune telling.

Even though I was thinking about being a writer, teacher, journalist, or spy, it turns out that I was learning a lot of lessons about work and entrepreneurship from my parents that have benefitted and shaped my career.

For most of my life up until I graduated from university, my mother was single and working. She was a secretary from the mid-70’s to the early 90’s for law firms, an eye doctor, and a university. (And I use the term “secretary” on purpose because that’s what it was called then.)

My mum worked hard, was smart and capable, got paid crappy, and had to deal with the kind of sexism that may seem like a cliché to us now but was common during that time toward a young, single, divorced woman in an office.

My father was a tireless, serial entrepreneur. In fact at 71, he’s still working it as VP of sales for an educational software company. While he started his career in social work, he decided early on he wanted a change, to work for himself.

So in the mid-70’s he moved to a rural area renowned for its terrible economy and started the very first recycling operation in the region. Over the the next 30+ years came other businesses and ideas for new ventures.

In the early 80’s he started selling Texas Instruments personal computers at a time when NO ONE had a computer in their homes. Then a few years later he became the first Apple dealer in his region, and this was way before Apple was the cool kid on the block it is today.

He also developed software to help doctors manage their billings and created a history program for elementary schools.

My parents have very different personalities, careers, and lifestyles and naturally I learned a great deal from them about life, as children do. But I’ve also learned some very specific things from both their career experiences in terms of how I approach work, business, and entrepreneurship.

My brother and me going off to work at our first jobs at my dad’s recycling company.

Iron Your Hoodie

This may sound like a silly business lesson but both my parents always look good. Not glamorous, not flashy, not expensive but they always looked pulled together and appropriate.

My mother said that there were tricks to make you stand out (or blend in, as the case may be) even if maybe you didn’t have the same money or background as the next person. Looking clean, polished, and professional was one of those ways. Good manners is one of the others.

I’d see her going out the door in the mornings - hair and makeup done, a smart, professional dress (bought on sale, of course), hose, and stilettos (oh, the 70’s). The way Mum dressed she likely looked ‘above’ her position but it gave her the confidence to command respect and professionalism at her job.

Even when my dad’s in his home office and likely isn’t going to see a client, he always puts on a nice sweater/shirt combination.

As a result, I’ve learned how to use my clothes to help set a tone for meetings and my own attitude. Depending on the client, on the situation, on the relationship I want to establish, I dress for that part. Job interviews, new clients, new co-workers, new partners, the bank.

I know office life is much more casual now, especially in the startup world, and I’m not suggesting I wear a suit every day but I am conscious of how what I wear and how I wear it can both affect how I feel about myself and how others see me.

In a business situation, those are important things to manage.

Give Them More Than They Asked For

Both my parents are really big on exceeding people’s expectations. In school Mum used to tell me, “If the teacher asks you to write 500 words, give them 750. If you’re told to show up at 8, show up at 7:45.”

Sometimes I would argue back that there was a reason a teacher would ask for only 500 words and you would get penalized for going over but I got Mum’s point.

The same with my dad. Just the other day we were talking about how he likes to get back to his clients before he said he would and provide them with a little bit more information or a little something extra than what they were expecting.

I remember when he sold personal computers in the 80’s there were lots of times he would drive over to a customer’s house in the evening to provide support (IMAGINE!).

It’s part of the reason why through all his businesses he’s had really great relationships with his customers and partners. They always appreciated the extra, it made customers feel looked after, and special. That Dad was taking care of business, their business.

This “extra” approach wasn’t lost on me. I’ve tried to apply it through my whole career - being extra prepared for meetings, doing background research, providing more detail in emails or briefings than was asked for, being flexible with clients.

I know that in business you sometimes have to monetize the extra or you can end up in costly situations like the dreaded scope creep but there are still ways to add extra value that doesn’t involve a lot of money.

Shockingly, sometimes just doing what you say you were going to do is perceived as extra by clients.

Don’t Take Shit

As I mentioned earlier, my mother worked as a secretary at a time when there was no such thing as a sexual harassment policy and there was little awareness if any about the inappropriateness of sexist comments and behaviour.

But being a young, divorced woman in a support role for professional men, she, like many of her co-workers, regularly experienced in real life the kind of fictionalized situations we watched on Mad Men. Sometimes subtle, often blatant, but it was there.

My mother has a strong personality and a good sense of herself so sometimes she was able to push back but because of the times, because she needed the job, there were other situations when she just had to let it roll.

This obviously isn’t my mother but I always loved the movie Working Girl as I imagined my mum rising out of her secretary role to be the CEO (and marry Harrison Ford)

This had a profound effect on me growing up and when I started working I vowed that I would speak up and speak out, whether I experienced sexism or rudeness or general disrespect happening to me, or to someone else.

Sometimes there’s been a situation that doesn’t really bother me but then I think about it happening to someone else who might not feel they have the power to speak up if the same thing happened to them. So I feel compelled to speak up on their invisible behalf.

Knowing I have the power to push back has given me confidence in business situations when someone has tried to make me feel small, to minimize my contribution, or to exert control over a situation they have no business controlling.

It has made me almost fearless. Not just in terms of fighting jerks in the workplace, but about almost everything. And feeling fearless is a really valuable and empowering trait when it comes to being an entrepreneur, owning your own business, or just trying to get move your career forward.

Be Nice

I know there’s this whole negative thing about nice, especially when it comes to business and I just don’t get it.

People have mixed up being nice for letting people walk all over you. They’re not the same thing at all.

My dad is one of the nicest people you’ll ever meet. He’s charming and funny and personable and polite and, well, nice. He treats everyone he meets with respect and he errs on the side of “we’re going to be friends” as opposed to viewing people as adversaries right off the bat.

His niceness set him apart in business. It’s what his customers remember about him. It’s why they continued to do business with him over the years. It’s how he’s built great relationships with industry colleagues and business partners.

At the same time, my dad’s no push over. He is sincerely a nice person but he has a line, that line may be farther away than most people’s, but he has it. And he won’t let you cross it, he won’t let people take advantage of him, he won’t let them be rude, he won’t let them be disrespectful.

If he thinks you’re not on the right track or you’ve done something wrong, he’ll tell you. But he’s no ‘tough son of bitch’ that many people think is the persona you have to adopt to be successful in business.

I’ve always admired this about him and I’ve watched how it has worked to his benefit in both his personal and professional life.

I seriously believe in the wise words of Mary Poppins when she said, “A spoonful of sugar helps the medicine go down” and I would put it on my “Top 10 Quotes That Have Inspired Me in Business”, if I were to ever write such a thing.

I don’t buy the business bully attitude of the Shark Tank’s Kevin O’Leary or the idea of being a “boss bitch”.

I believe you can be successful in business, be fearless in your attitude, get shit done, and still be a nice person.

My business mentor

Nobody Owes You Anything

Both my parents worked incredibly hard under difficult conditions to thrive, to provide for their family, and to achieve their own personal goals.

But I never, ever heard them blame someone else about the situation they were in. Or complain that they deserved better or that they were owed the same success that someone else had achieved.

Growing up with a single mum, I learned there’s no one else. You gotta do it yourself. You need to make your own money, know how to manage it, make the decisions, and deal with the consequences.

My mother was constantly striving to develop her career, to lift herself up. With two kids in high school, working full time, and looking after her own ailing mother, Mum decided to go back to university to finish her degree after a 20 year hiatus. She studied at night, on the weekends, in the summer, and she did it while somehow juggling everything else.

As a small business owner and entrepreneur in a deeply economically depressed area, my father faced constant challenges. I watched him pivot to survive long before pivoting became Fast Company’s word of the week.

He reinvented his businesses, he developed new services, he came up with new ventures, he’d call up strangers to talk potential partnerships. Some things failed, some things succeeded but I never heard him talk about his destiny as if it wasn’t under his own control.

Watching my parents work hard and be self-sufficient helped me manage my expectations when I started my own business, and in how I live my life in general.

I get that I am captain of my own ship. I am not Rapunzel waiting for my financial partner, or the government, or the collapse of the competition to rescue me from my tower of business challenges.

It’s up to me. And with that knowledge comes a freedom, even if sometimes it’s scary. Because when you blame other people for your problems, it gives them control over your life.

And ain’t nobody got time for that.

Don’t Settle for the Status Quo

If either of my parents had settled for their lot in life, things would be very different. First of all, we’d all be miserable because they would have stayed together in a marriage that wasn’t working.

And while there was a lot of pain and challenge for everyone associated with their divorce, I believe it set us all on a track to pursuing lives that make us happy. If there’s one thing I learned from their marriage and subsequent divorce, it’s that I refuse to accept unhappiness as my status quo.

As my parents rebuilt their lives separately, I watched them try new things: new businesses, new jobs, new partners, new hobbies, new attitudes. Not everything always worked out but they never stopped trying, reaching, and believing there could be more.

My father was always an early adopter of technology and he really connected with Apple’s philosophy of “Think Different”. He’s never been afraid to try something new, like quitting a steady government job to start a new business in a totally different town.

Or calling up a big corporation to pitch an idea for a new venture. Or developing software even though he had no previous experience.

And while financial security is understandably important to my mother, she’s always been proud of the ways my brother and I have explored life and taken risks, risks she wasn’t necessarily able to take when she was our age.

Learning there is life beyond the status quo gave me the guts to quit my well-paying, steady, but stressful agency job to go freelance. It gave me the confidence to buy my own small business.

It allowed me to encourage my boyfriend to quit his unhappy job to pursue being an artist. And it helped me be open to the opportunity of returning to work full time here at Proposify.

Not accepting the status quo is critical to the entrepreneurial spirit, and it’s also the key to a happier life.

Have a Sense of Humour

Last week I spent 7 hours at the hospital with my father while he had a procedure related to a very serious medical condition. I think people in the waiting area thought we were deranged because we laughed and cracked jokes to each other both before and after his operation.

You know what my dad said to me the following morning?

“Boy, that was a fun day yesterday!”

Our ability to laugh and make fun of a situation transformed what could have been a very stressful, worrying time into a day I will fondly remember. That’s not to say I wasn’t concerned, but having a sense of humour about it made it manageable and less unpleasant.

There are times when owning a business, or being an entrepreneur, can be extremely stressful. Sometimes it’s just not fun, it’s dark, it’s scary, and it sucks.

But finding the opportunity to laugh when you can and to lighten the mood isn’t going to make things worse. It might just give you a well deserved break so you can reset and get back to killin’ it.

PS My Parents Aren’t Perfect

Don’t get the idea that my childhood was the perfect business incubator. There are mistakes my parents made (so I did the opposite!) but I’m not going to talk about them here because I want to stay in the will.

But overall, I am really grateful for the inadvertent lessons learned from both my mother and father that have contributed to my topsy-turvy and incredibly rewarding career in business.

What I Learned About Business From My Single Mom & Entrepreneur Dad

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