How to sell stuff online when you hate talking to people (adventures in introverted entrepreneurship)

How to sell stuff online when you hate talking to people (adventures in introverted entrepreneurship)

I didn’t start speaking until I was ready for full sentences. I don’t like making mistakes and hate being laughed at.

Like most people, when I got into art or writing, I wanted my work to be “finished” before sharing it.

Even though I’ve learned to share work earlier to get feedback before committing to something, I still feel like most of my content is half-finished.

So it’s hard for me to share it. Not because I don’t think it’s good enough or people will hate it, that kind of rejection doesn’t really bother me, but because I don’t like talking about myself and am cautious to let other people share their stories (I read How to Make Friends and Influence People as a teen and it made me a good listener. Now I can pretend my social anxiety is a deliberate skill for building relationships).

HOWEVER, as someone who makes a full-time living online, some of these personality traits are not ideal.

In fact, I kind of suck at online business.

Not to say I haven’t had some success – I’ve learned a lot about content marketing and positioning my services, and especially about making friends online and creating viral content (those are probably my superpowers).

And I did it all WITHOUT advertising, or guest posts, or affiliates.

But I’m starting to realize that’s nothing to brag about. It basically means it took me a decade and I’ve always kept to a small playing field.

At the beginning of 2018, for the first time ever, I have scalable, passive income assets – which took about five years to get the hang of.

And now that I have them, I can scale and grow in a big way, but only if I take a deep look at the stupid things I’ve been doing and try to cut them out. This has led to a bit of a personal crisis. It’s like mastering the smallest diving board and then moving up to the super high and terrifying one and being afraid to jump.

I’ve started to realize how far I’m going to AVOID effective strategies that would mean less work and more money, like I’m determined to make things harder for myself. Now that I have some time to really focus on growth, I’ve built a pretty elaborate content marketing plan to fix some of the basics things I’ve been doing wrong for years. And I still feel like I need to make all my stuff “better” before I drive any paid traffic to it. And I’m aware of the massive resistance around advertising (putting my stuff out there in front of strangers.)

I’ve always said “someday, when I fix all my shit, and things are working, it’ll be AWESOME.”

But a lot of it has been mental resistance and procrastination because I didn’t feel ready.

Well, 2018 is someday.*

Here are some of the mistakes and insights I’ve been figuring out of the past few months. I hope they help you consider how to improve your own business or online platform.


#1 Giving up after the first try

Last night I was at dinner with friends and shared something exciting… that I’d sent out a couple pitches.

I don’t like to ask for permission or beg for favors, so I’m reluctant to ask for things unless I can prove considerable value.

But I DO have a sizeable platform now which isn’t being used for that much – since I rarely sell my own things (I haven’t emailed for about three months). We’re heading to Bali, so I wrote a pitch to stay at a nice resort at a discount. It’s a pretty good pitch; I mention how we’ve been featured in CNN for running writing retreats and if you Google “best writing retreats” I’m on the first page of results.

I also sent some notes on two nonfiction projects I’m working on to an agent (first time ever, scary stuff!). I’m happy self-publishing, but to reach the level I want to be at in a couple years, I need some traditionally publishing stuff, especially for nonfiction.

At dinner with friends at Saigon’s best ramen restaurant, I was feeling excited and proud that I’d actually done it – put myself out there.

My friend commented caustically, “maybe you should, I don’t know, send out more than just one pitch.”

There’s something to be said for showing up with consistency. I saw another author recently claim to hit the top #100 on Amazon by posting repetitively in Facebook Kindle Unlimited groups. I don’t think the tactic works because those groups are full of thousands of authors promoting themselves. What he did different was show up every day, for a month. In other words, he took a tactic that wasn’t working but did it better than everyone else by fully committing to it.

A related thought I’ve been mulling over, is a comment a friend of mine made when we were out in Saigon – in a new city, he said, you have to find a club and keep showing up. You can’t bounce around at every club in the city, making no relationships in any. The place and experience is about the people anyway, but the party won’t start just because you show up. You have to show loyalty, become a regular, get people to notice that you keep showing up here – that’s when they’ll start to look closer (plus it takes something like seven impressions to even make a dent, so no wonder posting once in groups doesn’t work at all).

I don’t like asking for permission or approval or free stuff. BUT – I need to decide on what I want and make it happen. First, I want to get as good and polished as I can, so I’m not asking for favors, I actually have something of value. But if I really want results, I need to send 100 pitches, practice and polish, and keep improving until people start saying yes. I’m not saying spam Facebook groups, but I am saying: find a place your readers are and show up every day.

The key to success is in the rejection. You need to aim to fail 99 times so you’re GOOD enough to score on the 100th try.

Don’t pat yourself on the back for reaching out to one person.


#2 Underselling

I don’t like to be pushy, or use hyperbole or false enthusiasm, so I won’t tell you this is a “once in a lifetime opportunity!” or “but wait, there’s more!” 

Instead I say things like:

  1. This MIGHT work for you, maybe.
  2. Honestly I don’t even want to be doing this…
  3. There are plenty of other cheaper/better options…

People want to know that THIS is the thing they need and it will solve all their problems.

BECAUSE: and this is a related topic – the opportunity cost of indecision is huge. I suck at travel, because I put everything off to the last minute, every time, and not only waste dozens of hours searching, but also end up overpaying in the end for whatever was left.

If I want to help people, I need to help them get through the frustration of choice paralysis and guide them towards making a decision quickly, so they can stop worrying about it or doing more comparative research. Being able to do that is as valuable as the actual product.


#3 Undercharging and overdelivering

I want everyone to like me. I usually offer to do stuff for free (for EVERYBODY) but then don’t have time, and then they get upset.

I usually charge “just enough” to pay me for my time, and maybe for the resources, which doesn’t leave anything for overhead, which means I can’t scale or grow.

Because my sites get traffic and there’s a lot of demand, I’ve raised my prices (on cover design at least), but I still feel like I’m “charging too much” which makes me bend over backwards, usually working with clients for months if not years (for free), instead of charging for small updates or changes. Personally, I like to do this. However, it’s also why I grew frustrated with client work altogether and decided to quit as much as possible so I can focus on my own creative projects. This is 100% my fault, I love my clients and want to help everyone, but I also need to focus my time on my most valuable projects.

Don’t charge what something is worth to you – charge what it’s worth to your clients. 

Something else I wrote about recently was how most bestsellers don’t make any money.

That’s because, even for a SUCCESSFUL launch, the bar is so low that most authors are happy breaking even… which means “yeah, I’m able to work really hard for months on a project for FREE.” In other words, instead of paying people to read your books, you’re earning your investment back. This is actually hard, and rare. And if you can do it, then you can also scale, so it is actually something to celebrate. But only if you can scale it, because you’re investing in your platform or list (otherwise, you’ll always need to spend all your money to reach new readers).


#4 Refusing to scale (services vs. products)

I’ve been trying to go from services to passive income products, which means… instead of someone landing on your site and deciding to hire you, there’s usually some kind of funnel. They sign up for something free, you educate by sharing awesome content, and then you make the sale with a limited time offer. I’m getting better at this, but there’s a lot of moving pieces.

Once thing I’m still doing wrong, is being insecure about my pricing, and offering SO many bonuses and extras that it devalues the core offer (people don’t want all the extra stuff, they want one solution that’s going to solve their problem). But the main challenge, is that I got into passive products so I could avoid client work, but I’m actually spending lots of personal time and feedback helping the people who join my courses. That’s fine, because I’m learning so much about how to make better courses and serve them better, but I’m also not growing or advertising or anything because I don’t have time for new clients (while also charging much less than I do for custom work or consulting).

This is a confidence issue: I’m not worried about it, because as I get more confident in the value of what I’m providing, I’m OK raising prices. I started book cover design at $150, then $300, $600, $1200 and $3000. I’m fine with pricing low and over-rewarding my first students. I always want to overdeliver and give personal help and feedback… but as long as I’m in involved in the solution, I can’t scale or grow my business.

My solution will be: cheaper stuff that’s DIY, and more expensive stuff with more personal help and feedback, although when I explained this recently to a friend, he pointed out it was obvious I didn’t WANT to do the expensive feedback stuff – that’s why I was quitting client work. I don’t HAVE to do that and if I’m not excited about it or it takes me away from great work I’m enthusiastic about, I should stop offering to do extra stuff because it’s easy for me or will only take a few hours.

My plan for the future, is a monthly, recurring membership site with all the resources I’ve built, or a more expensive package that included coaching and personal feedback. From 2019, I’ll charge at least $997 for anything that requires my personal response and feedback, and will focus on helping the people who are ready to see massive results.


#5 Doing everything myself

I’m not sure if this is really an introversion thing, but I have trouble letting go or asking for help. I just feel it’s so much easier for me to DO everything, especially if I’m better at it than everyone else, because team projects never work (especially for design!). But there are tons of critical things that never get done, because I don’t do them, and I don’t want to hand them off because I know what I want to do and they’ll honestly only take a few hours…

I don’t want to have to create a system process, or explain how or why it all has to be done a certain way, or feel disappointment when someone doesn’t do it the way I want it. (I’m terrible at working in groups, because I just want to take everything over).

BUT what I’m learning is, you get more than just the time back by working in a team: having partners increases motivation and productivity. It helps be clear and organized and make a process and instructions so anybody can do it. I am my own bottleneck, and there’s only so much I can do, so this is an issue I need to confront. I’d also LOVE to do some coauthoring since I’ve stockpiled scores of awesome book covers and plots but don’t have time to write them all.


#6 Paying to contact strangers instead of emailing my list

My plan has, for a long time, been this: get all my online funnels working so people show up on my list, go through my email autoresponder, and buy something – without me actually needing to email them or ask them to buy (this is the “hate talking to people part.”) I’ve done some product launches to my list, and I’ll usually announce something when it’s brand new (but only once – see #1).

Once my funnel is working, I can pay to advertise, bring in new traffic, and it’ll all work like magic without needing a single point of human interaction!

This is stupid, because:
A) I already have a big list that’s not buying, that already kind of know who I am. Some of them have been following me for years. It’s easier to sell to people that know you instead of strangers. BECAUSE you don’t have to work as hard to prove how cool you are, or get them to like and trust you (I’ve been building these relationships accidentally for years.) I’m not saying I’m going to start hard-selling, but I will focus on these things:

  • email more often
  • tell more stories

Just letting them know I exist and providing great content to brighten their day. When/if they need help with something, they’ll know where to find me. Some people may not be ready to buy now, but could be 3 months later.

Luckily, I can put a lot of this on autopilot too, once I get better at it. I should have months of autoresponder content set up. 

I should also:

  • email my list about my best ever content (to increase traffic)
  • write new content every week and send an email (consistency)
  • shoot for a weekly email with stories and helpful tips, which will also force me to create every day
  • ask my audience for support and engagement, comments, shares, etc.

Email list marketing via a brilliant email autoresponder + evergreen traffic funnels to build my list on autopilot + the best, lifechanging content they’ve ever seen and insane amounts of free and useful resources = passive income while actually making a huge difference and helping thousands of people with premade content, so I can focus on building MORE great and useful content for them.

When I have new books or projects out, they’ll be happy to support me because I’ve been supporting them for years.


#7 Thinking small

For years I’ve considered myself lucky because we can travel anywhere and make money online.

But a small part of me whispers, “this is enough.”

I just need enough so I have freedom to focus on my creative projects and write full time.

I’m happy making a few grand a month on my book sales because I’m doing pretty well.

I almost don’t want to draw too much attention to myself.

The problem is, I’m becoming the biggest fish in a small pond. I don’t want to be the smartest person in the room (that’s not an obnoxious brag, it’s a reference to a business idea that you can only learn and grow when you’re surrounded by more knowledgeable people).

I still want to focus on publishing, but more importantly I want to dive deep into the psychology of creative production, self-doubt, fear and anxiety – this is DEEP philosophy I studied for my PhD in Literature and it’s fantastic, but HARD. I want to introduce people to ancient mythology and Greek drama plays and French philosophers (it’s all really the same; philosophers just interpret classics of literature).

But this stuff is too fascinating not to share on a bigger level. 

So my new plans are: hit USA today bestseller with both fiction and nonfiction (single title).

I know how to do this, but I’ve never done it because I didn’t have a project I believed in enough yet, which also had a wide enough audience, and it takes a lot of long term planning and organization (planning, check. Organizing… not so much).

To launch a book like that, however, I need about 10,000 sales during launch week, and a significantly bigger platform to pull that off. Even though I hate talking to people on the phone, I actually love having interesting conversations with people, so I’m playing with the idea of starting a podcast. It may look something like this…  the podcast would be platform building to eventually launch the book.


I also want to keep investing in new tools and resources for authors (without paying for it all myself), and start partnering with others – guest posts or collaborative projects. I still feel like I’m learning, figuring things out, and I can be reckless with my experimentation.

I don’t have a polished or edited online persona – which makes me both immediately authentic, but also increases skepticism (who’s this “kid” and what does he know? I’m 38 by the way). I LIKE my online persona, and being fully transparent and honest, but I also want to MAKE BETTER SHIT.

A lot of my content is late night epiphanies or manic notes to self.

A lot of my content is rough and unedited. My YouTube videos must be torture to watch… lots of random wandering and tangents and ums… that go on for hours (I have over a million views but I doubt many people make it to the end of each video).

I want to be getting better about making high quality, amazing content that makes it EASY for people to learn from me, which will probably mean being deliberate about building epic thought pieces instead of hundreds of short fragments. (It would probably also take less of my time, if I stick with an outline or use slides or something)..

People are actually listening to what I’m saying now, and someone on YouTube pointed out that I’m building TOO much content. People don’t need more content, they need simple, entertaining solutions that help them solve problems and/or inspire them to keep doing creative work. I may also need to hire some help, to edit my videos or improve my platform, which goes back to #3 and #5 – I need to focus on earning more, with less of my time, so there’s enough extra to hire help AND scale with ads.


#8 Not using trust anchors

I’ve been featured on tons of podcasts, websites and media… but I don’t use the icons and logos. I also don’t say things like “bestselling author” just because I’ve hit #1 dozens of times. BUT – I need to give strangers a reason to listen. I’m reading Presuasion (will post about it when I’m done). But the idea is, people make snap decisions about you and your content before you open your mouth. 

Most people will leave immediately.

I need to use any tricks of the trade I can to slow down and listen to what I’m saying (as long as I’m also saying epic things…. see #7).

This is what I’ve got so far. Fun, right? I’d like to double this. I’m learning more about Presuasion and psychological trust indicators that can make a difference before people even start consuming your content.


#9 Relationships through stories

When I was a fine artist, I loved to quote Magritte and refuse explanation.

It does not mean anything, because mystery means nothing either, it is unknowable. The mind loves the unknown. It loves images whose meaning is unknown, since the meaning of the mind itself is unknown. 

“What’s my art mean to YOU?” I’d ask. I didn’t paint to mean things. I painted to bring life to strange juxtapositions I found funny or interesting. That didn’t work so well, because the value of art is arguably MOSTLY about the story (sorry for all the all-caps in this post, I don’t know what’s wrong with me today… probably because I’m at a cafe in Ubud without a mouse and it’s easier than trying to highlight and use italics).

Something cool I learned this week: people have to like you before they buy from you. And they want YOU to tell them what your product has meaning or value. It has to matter to them, but it’s your responsibility to explain why it matters (TIP: this is really hard. It’s so much easier to make something that has immediate and obvious value so you don’t NEED to explain it or talk about it – it should be a perfect fit for what they already want).

This one issue has probably been hurting me the most. (Or, at least, it’s my single greatest opportunity).

The first trick is getting in front of them. Obscurity is the enemy. I’m pretty good at this already.

The second trick is getting them to LIKE you.

Previously, I’ve done this with useful content. My email series is long and insane. I think most people respond, “WOW, there’s a lot of stuff here, I can’t believe it’s all free!” That’s great, but:

I’ve been telling other authors they need to see more things about themselves in their author bio or about page. “You need to mention anything you may have in common with readers. Nothing is trivial. Childhood stories, things you like and hate.” Pay attention to your favorite stories you tell at parties…. find a way to use those in your branding. 

You’ll see this is million-dollar product launch videos, where course creators will make their dog or cat part of their brand because it crates automatic sympathy.

My business should be about more than just useful content, because people don’t care about content.

With book covers, I say every cover needs a ‘humanizing element’ (not necessarily a character but at least an object or reference) because stories are about people. People don’t care about happens unless they’re already invested in the story.

That’s why most books and movies make the main protagonist immediately sympathetic by

  • taking care of a stray animal or child
  • defending the weak
  • having an object they care about from a lost/abandoned parent

My business needs to be about me, because stories get people to care, and the more they care, the more they’ll listen.

Luckily, my life has been pretty interesting and I have tons of travel stories I’ve never shared, which I’ll use to illustrate my content, like my 3 sketchy tattoos, or getting scammed by an art dealer in Malta, or getting robbed by a kid in Buenos Aires, or getting arrested in Egypt for buying a private tour of an off-limits tomb. My brand needs to be focused around my CORE values, which I figured out recently are freedom, adventure and creativity (with a pinch of Indiana Jones… the consummate scholar-adventurer.) Or even stories about crying over a girl at the airport, or playing lead in high school musicals, or how many scars I have from falling over trying to put on underwear (hint: it’s more than one).

I need to be personal and relatable, because I have so much knowledge to share and I want to help more people. But, as someone who doesn’t like to talk about myself and is somewhat of a recluse, I need to get better at this. (At parties, I’ll approach and stand by a group of strangers awkwardly but then leave without introducing myself because there’s no way into the conversation). 

I’m NOT saying I’m going to “try to be more outgoing.” If you’re an introvert, read Quiet by Susan Cain. Introverts are awesome. We don’t HAVE to be noisy, loud, aggressive or “more confident.” There’s nothing wrong with a healthy dose of social anxiety. But that doesn’t mean we can’t be vulnerable and share more of ourselves. We can do it in writing, and put the letter in a bottle, and throw it out into the sea (otherwise known as email marketing).

PS: Just by mentioning Susan Cain’s book above, I instantly created sympathy with all the other people who’ve already read and appreciate that book. This is why you should also focus on promoting/sharing books that have been influential to you, or create a “favorite books” page (it also helps with also-boughts).

NOTE: I had several people on Facebook recently tell me they HATED email lists and autoresponders, so they’d never have one themselves. I said it was important to build relationships with readers. They said: “why would I need a relationship with readers?”

This was me 10 years ago, at art galleries. I wanted people to buy my work and go away. I didn’t want to have a relationship with them.

But investing in the relationship is the key to building a loyal audience of super fans who share your work for you (which means, instead of paying to reach strangers who don’t give a shit, you can ask your fans to share your work for free).

As Seth Godin says, “Empathy is at the heart of marketing.”

The more they LIKE you, the more time and attention they’ll spend with your creative work, which will lead to increased satisfaction, and ultimately more positive reviews.

10: Emotional support

This is similar to the last point, but a little murky still in my brain, so let me do my best:

You can’t just talk about yourself. You need to stand back and let other people fill the space. You need to engage and ask questions. You can’t get people to like you by talking about yourself, but you can get their attention with story and reveal something personal and then get them to tell you something about themselves.

But mostly… if you don’t CARE about your audience, you can’t give them content they love, because you won’t understand what they need or appreciate. You can’t make them feel heard and accepted and appreciated. Why would you want to do that? Because that’s how you make friends. That’s how you build a tribe, so it’s not just you screaming your creative expression into the void. “I create, so I AM!”

The void doesn’t care.

You can do creative work without ever sharing it to anybody, that’s fine.

My definition of creative work is making things that matter to other people: it’s not art if it doesn’t resonate or create an emotional or cognitive imbalance, if it doesn’t affect. In other words, True Art is social. It doesn’t really matter if people LIKE the work, but the more people like and appreciate you, because you’ve made efforts to validate them, the more likely they’ll take time to at least take a look and try to understand, and they may be supportive of your work even if they don’t get it. 

Let me try again…

A video I watched this week said you don’t ever need to sell anything. You just ask questions and let them tell you what they want.

You let them sell themselves by listening to them.

You don’t defend or justify or PROVE that your product/book is awesome. You might not even sell your own products (the less the sell, the more people will want to work with you). People who try too hard (me) to sell lack confidence or experience. Unfortunately, this means everybody buys from more confident sellers, even if they’re overpriced or don’t have a good product that actually helps people.

My point:

I need to get a LOT better at building relationships AFTER people get into my funnel… there’s a term this week I learned call “hourglass funnel” and it kind of blew my mind. I’ve been working to get people into my funnel, but I didn’t consider that through a continuous, long term campaign to surprise and delight readers after they’ve already signed up or bought something from me, I can drastically improve the likelihood they’ll recommend me or share my content.

*I already planned to do a little of this, with bonus giveaways and things to bribe people into sharing, but the best bribe is great content and relationship building. So in my new autoresponders, I’ll make a massive effort to focus on building relationships/presuasion immediately after they sign up, and getting engagement right away, and standing out by being supportive and helpful.


For years I’ve been frustrated because real content isn’t as valuable as motivation.

I tell people how to do stuff. My tactics work. But my content can be overwhelming. Some people get behind and feel frustrated because they can’t keep up.

I need to:

  1. Make things easier to learn and consume – I tell nonfiction authors this. The content isn’t valuable unless people learn and take action, which depends on stories (to hold their attention) and relationship (getting them to engage).
  2. Let them know that it’s FINE to fall behind, that this stuff is HARD.

I’ve never really done that before. I don’t like coddling people.

My approach has been ruthless tough love: “Almost everyone fails. You will probably fail, because you’re doing everything wrong. But if you don’t want to fail… you can do this other stuff that you don’t want to do instead.”

While it might be honest, it’s not particularly helpful.

People pay more for and appreciate encouragement.

“You can do this! It’s quick and easy! Even if you have no skills and talent!”

The truth is, creative success takes years of sustained intention, practice, platform building and work.

It can get frustrating, and isolating. Most people question themselves and feel overwhelmed (trust me, I’ve been there.)

This is part of the process. I need to be more vocal about my own struggles (like how I was super depressed in January because I couldn’t force myself to write another novel after I’d just finished one). I need to share this, because people need to know it’s OK, even normal. And then I need to figure out how to help people deal with procrastination and motivation issues, and keep on making more great work.

I actually just joined a $300 mastermind that’s ONLY a support group, to help self-motivate into taking massive action (I have a lot of time and freedom now, but am having a lot of trouble actually doing the work, and I have SO MANY books I need to write).

I plan to get much better at dealing with the psychological resistance to creative work, and I have some epic books/posts about this stuff coming up (I just checked, I have over 80,000 words of JUST research and historical anecdotes).


More Resources

Make sure you watch this epic 2hour video on email marketing.

It covers a lot of the things I discuss in this post but in much greater detail; there’s also a list of some big email marketing wins you can implement immediately. It’s also basically a roadmap of my entire online business strategy going forward.

Do you like this post? Is anybody out there? Let me know what you think with a comment or share!

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