The call often ends on a note of appreciation. My conversation partner, now reacquainted, says, “Thanks for reaching out.”

It’s surprising to me how willing even busy people are to catch up. In the services business, it’s good to reach out to at least a couple of people per week. Staying top of mind is as much a part of the job as doing good work.

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The iPhone needed fixing, and procrastinating on it wasn’t useful. Deciding to do something about it was. Paying a little more wasn’t a big deal, especially compared to the business opportunities in front of me. I realized I could either continue to drain myself for a small expense, or let it go and focus on the projects in front of me. I had, unknowingly, engaged in maladaptive frugality.

For me, it started from a young age, during which frugality was framed as a virtue and mindless spending as, practically, sinful. During one of my parents’ anniversary dinners, they ate takeout, and my dad decided to use it as a teachable moment. What I took away: eating at a good restaurant was bad, taking out cheap food was good because it saved money. 

My parents grew up in Hong Kong, and the people there have a lot of useful stories about saving money. A writer describes being frugal in Hong Kong, “There are cultural and economic reasons why frugality runs deep here. Many families carry memories of instability—economic downturns, business failures, illness, or the pressure of supporting relatives. For others, the habit is inherited: parents who lived through leaner periods teach children to treat spending as a moral hazard rather than a tool.” 

Matthew Hung describes Hong Kong being colonized by the UK, “Engaging in the free market gave a freedom to those blocked from democracy by allowing them an alternative context from which to improve their own situation, albeit at the individual level rather than the collective level of citizenship.”

My parents carried that attitude with them to Canada, and I also grew up practicing and valuing frugality. It has been very useful at times (including being able to travel for less!), and very limiting at others. Here’s an example, which I wrote about a couple of years ago:

I have a hard time spending, to the point where I would often procrastinate on buying things that I know I’ll need in the future. And of course, I don’t have it when I need it because I didn’t buy it… so I decided to restrain my obsession with not spending. Make good systems-level decisions and give consideration/consultation to high impact decisions, and also be ok paying $30 to book an airline seat earlier. I plan to have fun spending my money in the future, so it’s time to start practicing now.

When you default to the lowest cost option without considering the drawbacks, procrastinating or hesitating on spending, or guilt tripping yourself about an essential expense or making a recoverable mistake, you’re engaging in maladaptive frugality. 

The most useful thing you can do is be mindful of it and try to draw yourself into the present moment. As Tim Ferriss asks, “What does your last year—not your childhood beliefs—tell you about where you might invest more for a higher quality of life?”

When you make frugality your servant, it can offer you freedom. When you make frugality your master—maladaptive frugality—it traps you and limits your possibilities.

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The speech was followed by a wide ranging Q&A session, which I also found very energizing. A portion of it was dedicated to writing to think, which inspired a LinkedIn post the next day. We also discussed boredom, and how boredom contributes to curiosity, as well as going all-in on creative work (or not!). 

I found out one of their kits comes pre-printed with a coffee stain on one of the papers, just to make it friendlier to write on.

It was a great opportunity to share more copies of Creative Doing, develop the speech, practice.

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“No, it’s going. It’s not working,” he replied. That distinction resonated with me. 

Many times, projects and practices won’t produce the results you seek right away. You will need to get it going before you can expect it to start working.

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If you make eye contact, wave, and say, “Excuse me,” you are off to a good start. 

Learn to ask indirectly. Feel out when to push and when to pull back. Know when to offer to put in some effort, and see if they may change their mind.

There are many indirect ways for someone to say no. Try not to be insensitive. Listen carefully.

Everybody feels a degree of discomfort when they need to initiate a conversation. Don’t let that feeling stop you.

When you experience rejection, be proud of yourself because you got closer to a yes than you would have been without asking.

“What’s the reason…” feels much easier on the ears than, “Why…”

When you don’t ask, you’re saying no to yourself. It will happen in spite of your best efforts. Be easy with yourself.

Always ask!

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With their experience, they can suggest more expansive possibilities than you could have imagined. All you have to do is one thing:

Ask. 

Always ask.

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Ryan decided he was going to communicate directly with fans in order to build a database. He released a new album, and made sure it was only available if you sent him a text.

Going direct meant more freedom and control, but it also took a lot of work, something that Ryan was never one to shy away from.

Initially, I participated as a fan. After I bought a couple of products and suggested ideas to him, he invited me to work with his team. I got a sense of how it felt both as a fan and an artist. I wrote more about the big takeaway: own your marketing, own your income.

I recently read about how streaming was minutes away from becoming obsolete. It reminds me of an essay my friend Danny, who was also on Ryan’s team, wrote over a decade ago about hacking the music industry.

The most useful thing I took away from all of this was the mindset: to add value to someone else’s life through media, create conditions for you to build new relationships and deepen existing ones (via text or email list, or even a blog), and to create new products and services that could add more value to their lives. 

While I didn’t have a huge fanbase like Ryan did when I was selling my first book, I had my friends and I learned to develop thick skin.

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As I continued promoting, more people I didn’t know bought it—a good sign of organic growth. Eventually, I signed a publishing deal with Holloway, took No Right Way off Gumroad, and expanded and revised it to become Creative Doing. 

As I’m writing this, over 5,000 people have bought copies (here was a post from 3,000)—and I’ve easily given away hundreds of gift copies to friends and strangers.

While I have the customer data of maybe 10% of my readers (the ones who bought through the Holloway reader), many have also bought through Amazon or other platforms. I no longer know the vast majority of them. But if my friends hadn’t been so supportive to start with, and contributed to my book’s sales history, maybe I wouldn’t have felt the confidence to approach Holloway.

If you’re looking to launch something new, there are many worse places you could start with than friends. You already know them, they trust you, and they want you to win. Bring it up in 1-1 conversations. Share on your social networks, more than once.

Be clear that you’re not obligating friends to buy. Say it and leave it in the wind. Whatever they contribute is an expression of their generosity.

My new work, The Consistency Journal, is available for pre-order. Many of my friends, once again, have contributed. Thank you.

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When you consider performing a song on stage, in front of an audience, the conditions change. It wouldn’t feel so natural to do that for most of us. Even if we did, we would want to practice and prepare before we performed.

Scribbling on scrap paper is easy because you were planning on throwing it out anyway. Scribbling on a new piece of blank paper can feel more intimidating.

One shortcut is to turn a new piece of paper into scrap, by putting a mark on it. 

The friendlier a surface is, the easier it is for you to express yourself. 

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You may feel sad about it, or even grumble occasionally, but you don’t need to let it stop you.

You can take yourself seriously. Do work and hold it to a high standard, as if you were your own boss. Deliver as much as you can, even if it means showing up early or staying late. Bring a positive attitude. Keep your promises. Take on as much responsibility as you’re capable of. Accept and work through the tension of contradictions.

Take your work seriously. Don’t take your ego so seriously.

When you do, and you hold yourself accountable for your actions, other people naturally start taking you seriously as well.

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