10 Lessons in Entrepreneurship From a Business Owner of 20+ Years

Truth bombs from a Hawaiian-shirt-wearing father about working for yourself.


Brooke Harrison

2 years ago | 7 min read

Every day, my dad goes to “work” in our guesthouse (his office). He wears Hawaiian shirts and takes a long bike ride every Thursday morning.

He’s a small business owner, a web developer, and he’s worked for himself for the 24 years I’ve been alive. He gave me the entrepreneurial bug. I’ve always been impressed with his flexibility and control over his schedule.

I’ve dabbled with the entrepreneurial lifestyle, but it wasn’t until 6 months ago (when I was laid off due to COVID) that I decided to go all-in on my dream of working for myself.

Well, it hasn’t been the straightforward path I thought it’d be. (Is it ever?)

For the first time, I’m beginning to understand the lessons my dad has taught me for years. In these past few months, he’s been an invaluable resource and mentor as I’ve worked to get my copywriting business off the ground.

Here are 10 truths he’s taught me about entrepreneurship:

1. Things Are Never as ‘Good’ or ‘Bad’ as They Seem

I thought (mistakenly) that I’d be less stressed after leaving my 9 to 5. My previous job was fast-paced, demanding, and high pressure. I often found myself working in the evenings or weekends to catch up. I thought the anxieties and fears would lessen.

Now, I’m the only one responsible. I may not stress about pleasing my boss, but I stress about finding work, pleasing clients, and finding decent (but affordable) health insurance.

When it comes to business, things are never as “good” or as “bad” as they may seem. And if you allow your emotions to be dictated by the ups and downs of the lifestyle, you’ll burn out quickly.

2. The Future Work You Want Is Already Right in Front of You

I never understood why my dad would say things at the dinner table like, “I don’t know what comes next; the work is drying up. A few months from now, I might not have any clients.” And then literally a week later, “I’ve got a big project; this will keep me busy for the next year.”

But now, I get it. Some days I sit at my desk and feel anxious that I’ll run out of things to do. And by the next week, I’ve got two new client projects I didn’t see coming.

The work will come. But you have to plant the seeds.

Keep your eyes open for new opportunities. Talk about what you do with friends and family. Expand your network. Do your best work for your current clients. After all, your former and current clients are your best source for future work.

3. No, You Don’t Have 8 Hours a Day

This is something my dad likes to say when I feel guilty that I have “so much time” on my hands and can’t seem to get things done. He’ll point out that I don’t truly have 8 “available” or “workable” hours in a day. Nobody does.

We’ve got to stop beating ourselves up for “failing” to cross off the twenty items on our to-do list. Not when we face interruptions, distractions, and unexpected (but unsurprising) emergencies.

It’s Monday morning — take a look at your calendar. How much of your time is already scheduled? As in, how much time do you owe your clients? How many phone calls or meetings are on your calendar? Don’t forget to block off time for researching new opportunities or pitching new clients and projects.

And how much time is left for you to tackle all the other things you need to get done?

You don’t have 8 hours a day. If you’re lucky, you might have 3–4 productive hours. It’s only when you’ve acknowledged this reality that you can strategize how best to use that time.

4. Force Yourself to Learn Every Day

A great plan, product, or service today won’t be the same two years from now. If you want to be competitive in the marketplace, you have up your game to meet demand.

My dad says this is a balancing act — on the one hand, you’ve got to look forward so you can stay ahead and continue to evolve. On the other hand, you have to focus on the present and keep your existing clients happy.

Continue to provide value and anticipate what your clients will ask for in a few months or a year from now. You want to be the one to meet their needs. Keep an eye on what’s happening in your industry.

When you work for yourself, you’re responsible for your continued education. There are no more work-funded retreats, training, or conferences.

Ask yourself, what do I need to learn to provide more value?

5. Don’t Pay for Expensive Clothes, Invest in Your Business Instead

A lot of people who meet my dad think he’s a cheapskate. He drives an old Honda CRV. He’s not a real snappy dresser. (Please recall the aforementioned Hawaiian shirts. Typically paired with basketball shorts.) In general, he’s financially conservative.

But when it comes to tools, resources, or furthered education, my dad appreciates quality. As a web developer, this means he has a powerful Macbook and monitor. His workspace is optimized for his comfort and health. In his free time, he might learn a new programming language.

You will never regret learning new things.

These types of investments — though, yes, sometimes expensive or costly — will pay off in a big way down the road. When you invest in yourself, you give yourself the tools to go further, push harder, and ultimately be more successful.

“Ultimately, there’s one investment that supersedes all others: Invest in yourself. Nobody can take away what you’ve got in yourself, and everybody has potential they haven’t used yet.” ~ Warren Buffett

6. You Can Change the Narrative

Titles are meaningless. As an entrepreneur, your job is always in flux. It’s unlikely that you do — or that you are — just one thing. Gone are the days when your role at your 9 to 5 job fit neatly in a box. Entrepreneurs do it all (because we have to).

You control the narrative. Call yourself what you’d like.

I can be a “freelance writer,” or I can be a “professional writer.” I could be a “content strategist” or a “writing consultant.” Yes, it’s true that our titles help us communicate to others what we do. So does our work.

As long as you’ve got the skills to back it up, who says you can’t change the rules?

Our family still doesn’t quite understand what my dad does. He’s a web developer, an auditor, a consultant. Somehow, someway, he’s made it work for the past 20-something years. He could care less if he’s got a job title that people understand.

7. You Don’t Always Have to be the ‘Best’

There are plenty of writers with more experience and more talent than me. So I have room to grow. Luckily, this doesn’t seem to dissuade my clients.

If you can’t compete in terms of experience, make up for it in professionalism and personality.

Remember, we’re just people. Clients want to work with you — not the cardboard cutout of your resume or LinkedIn profile. They want to know that you have a personality, that you’re easy to work with, and, yes, that you can get the job done. But in that order.

You may not have a Master’s degree or a fancy certification or 20 years of experience, but you build credibility by treating your clients well and doing your best work (not “the” best, but your best). It will pay off.

8. Life Is Too Short to Work With People You Don’t Want to Work With

Not all clients are created equal.

Speaking as a beginning freelancer, I know it’s hard to even entertain the possibility of turning down work. You don’t want to say “no” because you need to get your name out there, and you have bills to pay.

Luckily, I have a seasoned entrepreneur in my corner who has given me the following advice: No amount of money is worth the headache of a difficult client.

Life is too short to work with difficult people. When I worked for a marketing agency, I didn’t have the luxury of “choosing” my clients. There was no escaping the nasty calls or emails from rude and demanding clients. Truly, is it worth the stress, anxiety, or pressure?

You may not think it’s a big deal, but it takes a significant toll on your physical and mental health. Save your time and energy for the people who are thankful for the value you can provide.

9. Finding A Work-Life Balance Is About Your Priorities

Do you feel guilty when you’re working, and guilty when you’re not?

This is the strange phenomenon of the driven entrepreneur. Entrepreneurship can blur the lines between “work” and your personal life. It’s difficult to draw boundaries.

My dad has taught me that even busy entrepreneurs can achieve a healthy work-life balance. It’s about identifying your priorities. What’s most important to you? Are your actions in line with those priorities?

My dad puts our family first. We have dinner together every night — he has never skipped family dinner to work late. He doesn’t work on Sundays. These are decisions he made a long time ago.

It’s truly that simple. People think you have to make “sacrifices” to be an entrepreneur. I call it “compromise.”

As a family, we understand that the flexibility dad enjoys as a small business owner has its tradeoffs. He has the occasional work emergency in the evenings or during vacation. But at the end of the day, there’s no question — my dad knows how to make the tough choices because his actions are driven by his priorities and his principles.

10. Only You Can Define Success

There is no “measure” or “standard” for success. As an entrepreneur, the sky’s the limit.

There are people all over the world who make this lifestyle work. Older people, younger people, married people, single parents, and people without a fancy degree. “Success” looks different for every one of them.

Only you can define what “success” means for you. And, honestly, your idea of success will likely change many times over the course of your life.

People probably don’t think my dad fits society’s idea of a “successful” entrepreneur. And yet, he’s been self-employed for 20-something years. We’re a middle-income family without debt. We feel thankful for these blessings every day.

He doesn’t need to be a millionaire to be a “successful” entrepreneur. My dad is happy bringing in enough work to comfortably provide for our family and take the occasional mid-day bike ride.

When you know what success means for you, and what makes you happy, there’s no pressure to live up to anyone else’s expectations. There is no timeline. There is no “falling short.”

There’s only the satisfaction in finding meaningful work and shaping your own future.


Created by

Brooke Harrison







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