7 Things Steph Smith Taught Me About Creating

Dillan Taylor
8 min readMay 20, 2024

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How to get started, keep going, and the one thing you can’t forget.

Our creator community just interviewed Steph Smith. ☝️

She’s a serial creator with…

  • a sick blog​
  • loads of valuable courses & books (Internet Pipes and Doing Content Right are my favs)
  • a huge Twitter audience
  • 2 podcasts — a16z and Shit You Don’t Learn in School
  • too many cool projects to list here

I had to take a few breaths when introducing her on the call.

Here are my 7 biggest takeaways from our hour-long conversation.

1) Instead of trying to “be a creator,” just make cool and helpful stuff.

Traditional content creation wisdom tells us to niche down hard and fast. i.e. Pick a small group or category of people and be the best person to serve them.

Steph definitely uses her unfair advantages: intense curiosity, worldly experience, programming & marketing skills.

But her work has served a wide audience with a variety of interests:

  • tech
  • remote work
  • entrepreneurship
  • travel
  • unique Reddit communities

Putting her into a box is difficult. Other creators can be summed up as “Call of Duty streamer” or “conservative blogger.”

But when I describe Steph’s content to others, I say something like:

“She makes lots of practical and well-crafted guides on how to do things on the internet better…But she also does other stuff.”

Many creators who join Grindstone are trying to “make it as a creator.” But Steph seems to follow a different process:

  1. get really good at something
  2. people wonder how you do it
  3. explain it to them in a simple and digestible way so they can repeat it on their own

Her content answers questions like:

  • How do I start and grow a blog?
  • How can I work on several projects without burning out?
  • What can I do for remote work outside of tech?
  • What are the coolest places to travel as a remote worker?
  • Which industries make sense to start a business in?

She doesn’t try to “hack the algorithm.” She just lives a cool life and shares her best stories and lessons along the way.​

2) Use A.I. as a thought partner.

You don’t have to be a prompt engineer or a techie to use artificial intelligence.

I’ve used ChatGPT to help me create podcast episode names, newsletter topics, and an outline for Grindstone’s Creator Crash Course (coming soon).

I rarely use its exact ideas. But they always spark something in me that I wouldn’t think of alone.

Steph used it to brainstorm ways to make in-person meetups not suck. But my favorite thing she asked ChatGPT is:

“Explain dark matter to me in the voice of Spongebob Squarepants.”

In her mind, the hardest thing about using God-like technology like this is remembering to use it.​

3) Start your career by doing mind-blowing work for people…for free.

During the Q&A, one of our writers asked Steph for tips for a new copywriter.

“It’s not fair or equal,” she started. “But do free work a few times exceptionally well. The kind of exceptional work you absolutely should be paid for. What can you create for your target clients where it’s a no-brainer for them to work with you?”

(Uncle Alex has a brash short video on this topic.)

I started my coaching business by coaching my friends for free.

For three reasons:

  1. I sucked and had no clue what I was doing
  2. I needed improvement and experience more than I needed money
  3. It made it 10x easier to get testimonials, referrals, and paying clients

Now I get 2–10 emails per week from people asking for coaching.

It’s a tough pill to swallow for new freelancers, creators, and entrepreneurs.

But in the early days, you need practice and credibility. Prove that you are undeniably good, and the money and customers will inevitably come.

4) Make stuff so good, you never need to ask people to “like & subscribe.”

Adding calls to action (asking people to follow, comment, like, etc.) reliably increases the likelihood of those things happening.

But Steph offers a warning…

“If there’s a big gap between the results you get naturally vs the results you get when you ask for them…you need to ask why that is.”

My newsletter for example.

I used to spam my friends to ask them to subscribe. Many of them would.

But that’s quite different from other friends who discovered I had a newsletter and subscribed on their own because it sounded captivating. I didn’t need to coax them into doing anything.

Now let’s look at an extreme example: asking people to “follow for follow.”

Screenshot from a creator Facebook group.

It’s understandable for brand new creators. But it’s the worst thing you can do for your content.

Every successful and sustainable creator has an army of true fans — people who can’t wait for their next thing to come out.

Asking folks (who don’t care about your stuff) to follow you does not grow your channel. It damages it.

If you convince 100 community members to subscribe to your YouTube channel, say. You now have 100 subscribers who won’t watch a single video you upload.

Now YouTube thinks your own subscribers hate your content, and it certainly won’t promote those videos to anyone else.

We want true fans, not empty numbers.

Or, as Steph told us:

“There’s a difference between being a creator people follow and being a creator people respect.”

5) The true cause of burnout.

According to Steph:

“Burnout is never a function of the amount of work you’re doing. It’s a function of the difference between how much work you’re putting in and the progress you feel you’re making.”

This was exactly what I needed to hear as a guy who burnt out a few times. My exhaustion always comes from working on too many things, not working many hours on one thing.

Her insight poses a useful question:

How can I ensure I make a ton of progress on one thing over the next week?

If it’s impossible to do that, I’m working on too many things and something’s gotta go.

6) Control when a project is “ongoing” and when it is “done.”

When asked how she starts and completes so many projects without burning out, Steph shared a simple strategy that blew me away.

“I’ve got a bunch of things that exist. But they’re not all active projects.

Most people will start a project and just have this open-ended thing they think they have to keep addressing. But if you set very very concrete, almost irrational timelines…that can help you dramatically.”

Her examples:

  • the book: finished in seven weeks
  • Internet Pipes: done in less than two months
  • the podcast: uploaded in seasons and recorded in batches

“With Doing Content Right…I wanted to say something. I got it on paper in seven weeks. And for the most part, I never thought about it again. And that was designed intentionally.”

Customers even asked her to launch a paid Doing Content Right cohort. She declined for two reasons:

  1. The goal was not to milk this project for as much money as possible.
  2. She just wanted it done.

It could’ve easily made her tens of thousands in extra income. But she let it go to have more time and brain space.​

7) You don’t have to grind your face off. But work on stuff that makes you want to.

I asked Steph the closing question I ask most creators…

What would you say if you could give yourself one piece of advice when you first started creating?

“It’s something I tell my husband every day,” she smiled.

“Don’t forget to have fun. I know it’s so cheesy.

But what the hell are you doing being a creator if you’re not enjoying it? If you’re sending cold emails, how can you make it kind of hilarious? How can you turn drudgery into something you look forward to?

Don’t go a full day without having fun at least once.”

We ask similar questions in Grindstone:

  • How can you make it easy as possible to work as hard as possible?
  • What would this look like if it were easy and exciting?
  • What would ensure you’re still working on this a year from now?

Steph took us through her workflow.

“I don’t agree that you only have four good hours in a day. I can grind on a day I’m inspired for 16 hours and get a lot done.

But sometimes I try to grind for 16 hours and something’s really not jiving and it’s a complete waste. Those are the days I wish I just did the two hours of work.”

Do something that allows you to go into God Mode and unlock your superpowers. But don’t expect yourself to be in that state every day or even most days.

In summary:

  1. Don’t try to “be a creator;” just make cool things that help others.
  2. Ask ChatGPT to help you brainstorm.
  3. If you help 100 people for free, very good things will happen.
  4. Be a creator people respect, not just one they follow.
  5. Burnout happens when you work a ton but make little progress.
  6. Avoid ongoing projects; set a clear deadline and shut the door when it’s complete.
  7. Never forget to have fun.

BIG thanks to Steph for sharing her time and energy. 😇

Check out her plethora of goodies on her website.

If you want to follow my journey in growing Grindstone, get lessons from top 1% creators, and join me as I travel the world with my laptop…

Find me on:

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Dillan Taylor

Helping creators do their work, make better content, and grow an audience.