353: Are Successful Entrepreneurs A Product Of Tiger Parenting?

Podcast: Download (Duration: 17:12 — 31.8MB)

Succeeding in business requires doing work you actively dislike, sticking with problems long past the point of frustration, and building habits sustainable enough to last years. Everything is unpleasant at the start, and your capacity to endure that period is what determines how far you get.

In this solo episode I look at three lessons from how I was raised and how each one maps directly onto running a business.

Below are all three: why you have to get used to the grind, why being challenged is what builds perseverance, and why habits beat intensity.

Key takeaways

• I dislike writing and publish weekly anyway. It is a means to an end.
• People dislike what they are bad at and start enjoying it once they improve.
• Most excuses are about skills, not obstacles. Not being good at marketing is not a reason.
• Never being challenged produces fragility. Failing early is what teaches persistence.
• My blog earned nothing for three years. Traction came only after email marketing.
• Break big goals into daily pieces. 20 words a day beat one large summer target.
• Consistency beats intensity. Most people burn out launching before they build anything.
• Praise for easy wins is worthless. It removes the reference point for real accomplishment.

Lesson 1: You have to get used to the grind

Every successful venture has an unglamorous backstage, and being willing to work through it is the actual differentiator.

My Wife Quit Her Job is successful by most measures. There is a loyal readership, a course, an annual conference, a YouTube channel, and now TikTok.

What sits behind that is work I do not enjoy. I have never liked writing and I force myself to publish a 3,000-word article every week, and I still dread Sunday mornings.

The reason I do it is that you cannot run a blog without content, and the benefits of the business substantially outweigh my dislike of the task.

Sales and marketing are the same. I am an engineer by temperament and delivering a sales pitch during a monthly webinar does not come naturally, and I do it because the business requires it.

Why people dislike what they are not good at

The pattern I notice with my own kids is that disliking an activity and being bad at it are usually the same thing.

As they improve, the dislike fades. Getting past the initial period of being bad is what changes the relationship to the work.

That applies directly to business skills. Marketing was not something I enjoyed either, and competence made it tolerable and eventually interesting.

The excuses that are actually skill gaps

Most people who say they have tried everything have not, and the reasons they give are descriptions of skills they have not built yet.

The pattern is consistent. Someone reports that they have tried everything and sales are not coming. Their site shows no research and no real effort, and specific suggestions produce excuses rather than action.

These are real responses I have received:

• I am not good at marketing, it is not my cup of tea.
• I am a horrible writer, I cannot write good copy.
• I am terrible with tech and do not want anything to do with it.
• I want to run an online business but I am not interested in learning anything about the web.

Every one of those is a thing you learn rather than a thing you have. Running a business requires marketing, running a blog requires writing, and running an online business requires understanding websites well enough to not be helpless.

You do not need to be an expert at any of them. You need the basics.

Lesson 2: Being challenged is what builds perseverance

Never being challenged early produces confidence that collapses at the first real difficulty.

The mechanism is that if you have never failed, you have no evidence that difficulty is survivable, so adversity reads as a signal to stop.

School came easily to me as a child, which meant good grades without effort and teachers treating me as unusually capable. The result was a cocky kid with no experience of struggle.

My parents sent me to an accelerated summer program that thoroughly humbled me. Everyone was smarter, the concepts were unfamiliar, and I wanted to go back to being top of my class somewhere easier.

I did what most twelve-year-olds would do, which was panic and refuse to return.

What my father did next is the part that mattered. He walked through the problems with me and watched me struggle without ever giving me the answer, encouraging me to talk through my reasoning aloud and offering hints only when I stalled.

What I learned was that sticking with a hard problem long enough eventually produces a solution. That is the transferable skill.

How perseverance actually shows up in business

Both of my businesses required staying in far past the point where quitting would have been reasonable.

Our ecommerce store performed badly for the first several months, until I found AdWords and learned to use it properly.

My blog earned nothing at all for roughly three years, and gained no real traction until I learned email marketing.

The general form is that if you persist long enough you eventually find the thing that works, and you have to still be there when it happens.

The failure mode I see most is people signing up for my course and never watching the videos, asking questions, or attending office hours, then expecting results.

Why unearned praise is counterproductive

Compliments for things that came easily remove your reference point for what real accomplishment feels like.

My parents rarely complimented me, and a report card of As with one B produced a question about the B rather than praise for the rest.

The effect was setting the bar somewhere I had to reach for. Straight As were the expectation rather than an achievement.

The other half is what makes it work. When I did accomplish something genuinely difficult, the praise arrived and it meant something precisely because it was rare.

My own version of this is refusing to give false compliments to my kids. Praise for a real accomplishment is worth something, and praise for showing up produces overconfidence that fails on contact with difficulty.

Lesson 3: Habits build discipline

Consistency produces results and intensity produces burnout, which is why the schedule matters more than the effort in any given week.

My mistake as a new parent was assuming incentives would work. I offered my daughter a large stuffed animal for learning a set number of vocabulary words over a summer.

She wanted the toy and the task was overwhelming as a single goal. She tried to cram hundreds of words into a couple of days, got frustrated, and quit.

The fix was breaking it into daily pieces. Twenty words a day after camp, with me explaining each one and quizzing her at the end of the day, plus deliberately ridiculous sentences to make them memorable.

She learned nearly 500 words by the end of the summer and was genuinely surprised by her own progress.

Why consistency beats intensity in business

Most people start at an unsustainable pace and exhaust themselves before the business has had time to work.

The pattern is spending so much energy on the launch that nothing remains for the years of ordinary work that follow.

What I tell my kids applies exactly: if you want to be good at something, put practice into your regular schedule and commit to maintaining it indefinitely, expecting to stick with it for at least a couple of years.

The reason patience is required is that results lag effort substantially. Small incremental improvements compound into visible gains, and the gap between doing the work and seeing the result is where most people quit.

The underlying argument

My view is that we are all considerably more coddled now, and that wanting quick wins and constant enjoyment is incompatible with how anything difficult actually works.

Enjoying a win requires the difficulty that preceded it. Without that contrast there is nothing to enjoy.

The practical version: prepare to do what you do not want to do, and to learn what you do not want to learn.

Everything is bad at the beginning. Your ability to tolerate that period is what determines whether you get to the part that is not.

Frequently asked questions

How do you push through work you dislike in business?

Accept that it is required rather than optional. I dislike writing and publish a 3,000-word article weekly because a blog cannot exist without content. The benefit of the business outweighs the dislike, which is the calculation that makes it sustainable.

Why do people dislike certain business skills?

Usually because they are bad at them. Disliking an activity and lacking competence at it tend to be the same thing, and the dislike fades as skill improves. Marketing was not enjoyable for me either until I became competent at it.

What separates people who succeed from people who quit?

Willingness to stay in past the point of frustration. My ecommerce store performed badly for months until I learned AdWords, and my blog earned nothing for roughly three years until I learned email marketing. Both required still being there.

Why does being challenged early matter?

Without experience of failing, difficulty reads as a signal to stop rather than something survivable. Struggling through hard problems as a child teaches that persistence eventually produces a solution, which is the skill that transfers.

Does praise help or hurt?

Praise for genuine accomplishment helps and praise for easy wins removes your reference point for what real achievement feels like. It produces confidence that collapses on contact with actual difficulty.

How do you make progress on a large goal?

Break it into daily pieces. My daughter failed at learning hundreds of vocabulary words as one summer goal and succeeded at twenty a day, finishing with nearly 500 words. The same structure applies to building a business.

Is consistency or intensity more important?

Consistency. Most people start at an unsustainable pace and burn out before the business has had time to work. Commit to a schedule you can maintain for years, and expect results to lag effort substantially.