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People ask me how I post every day.

The answer is less glamorous than they probably imagine, especially in the early days.

Exhibit A: The ski trip last winter. Everyone around the table, Mexican Train tiles clicking, gin flowing, genuinely good chaos. Me in the corner with my laptop, sweating over the next day’s post.

Then Exhibit B: Disney World, family vacation. Up before anyone else, squinting at my phone in the dark, reading my draft back to myself to confirm it was relevant and, more importantly, coherent.

I started posting every day in January 2025 with a simple theory: a daily habit is easier to keep than a sometimes habit. I’d read enough from creators who’d been at it for years to believe them. So I decided to test it myself.

I had no content calendar, no strategy, and honestly no real sense of what my voice even was.

Just: post something today. Do it again tomorrow.

The compass

Before I write anything, I check my content pillars: staying visible, building the pipeline, and what AI can do versus what only you can.

I think of the pillars as a compass.

When I’m stuck, I pick one and start there. It narrows the field from “anything in the universe” to “something I actually have a thought about.” That one step has saved more blank-screen mornings than I’d like to admit.

Where things live

Apple Notes is where ideas land first. A half-thought on a walk, something someone said in a meeting, a phrase I don’t want to lose. I don’t organize it, I just get it down before it disappears.

Notion is where things develop: drafts, outlines, a running content bank. Really, a place to think without publishing.

Google Docs are for anything longer, like this newsletter. There are no elaborate workflows. Just somewhere to put things so I don’t lose them (and oh, do I lose them.)

Post 47

It’s a funny thing to establish “your voice” when you use it literally every day.

But writing it down is a different animal.

And it doesn’t show up until somewhere around post 47. Or post 93. Or 200.

My early posts sound different, noticeably so. Yours will likely evolve, too, which is the process working exactly as it should. You start with the practice, stay consistent, and dial in the voice from there. (That “you fairy dust” that everyone wants.)

The hard part is doing it when you don’t feel like it and when nobody’s watching yet. Before you’re sure it’s working.

You do it anyway.

Occasionally, from a ski chalet, while your friends are having a significantly better time.

One more thing

This is what it looks like in the beginning, and even still some weeks.

There’s more to the game: social selling, consistent engagement, and figuring out where AI actually fits. I’ll be writing about all of it.

For now, one question: what’s working for you, or what’s getting in the way of starting?

✈️ Carry On
with Pamela Wilton

Stay in touch, stay visible, stay helpful.

Increase your luck surface area.

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Do you believe in luck?

Some people do. Others don’t.

Either way, I can confirm that there is a concrete formula for increasing luck.

When I was 15, I had the opportunity to go on a class trip to Europe.

My parents said no, and I completely understood. Resources were tight with a family of 4 kids. It simply wasn’t in the cards.

But I still told people about it. Socialized it a bit.

My feisty grandma caught wind of it and contributed. I picked up extra work. My parents chipped in.

In the end, I slid my deposit to Mr Whitelock right at the deadline.

I travelled to Europe!

And when I came home, all I could think about was how to keep doing this.

That trip was lucky and also… it wasn’t.

It was the first time I expanded my luck surface area without realizing that’s what I was doing.

The Formula

Fast forward to last month.

I gave a speech about exactly this concept at a Toastmasters International Speech competition and walked away with third place at the Division level.

The speech is called “Who Wants to Get Lucky?”

It keeps coming up, and I think about it all the time.

Plus, it’s so simple.

The concept breaks down into 3 simple parts.

1. Doing

Try things before you feel ready. Say yes to the collaboration, the speech, the new skill. You don’t need one perfect project. You need 100 small experiments.

For me, this has looked like taking on different roles and joining new communities.

Signing up for competitions. Trying out for frisbee teams.

2. Positioning

Get closer to where exciting things happen. Exciting for you! Become known for something so people think of you and go to you.

This is when I stopped being a generalist and started specializing.

International accounts. Long sales cycles. Relationship-driven business development.

The work that gave me travel opportunities.

3. Telling

This one always feels like the hardest part.

Early on, it was conversations with mentors. Advocating to be in client-facing roles despite the dull ache of imposter syndrome.

Later, it was sharing ideas online.

(I’ve now posted on LinkedIn for over 460 days straight!)

Also, just ask.

People won’t know your dreams until you tell them.

Long Game

The formula:

The more you do + the more you position yourself + the more you tell people about it = the bigger your luck surface area.

This isn’t a 30-day sprint, as it compounds over years.

But it works if you stay in the game long enough.

It’s been one of the most exciting parts of building this business - helping others expand theirs.

Which one of the three do you need to work on most right now?

I’d love to know.

✈️ Carry On
with Pamela Wilton

Stay in touch, stay visible, stay helpful.

Increase your luck surface area.

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I was in Ottawa last week for an AI event with the Canadian Chamber of Commerce.

A full day of panels, breakouts, huge thinking, and honestly … pretty great food.

At some point during a session, this quote appeared on a slide.

90% of your skills just dropped to zero

Kent Beck is a super smart software engineer. The guy who invented Extreme Programming. When ChatGPT launched, he tried it and said:

I can’t stop thinking about this.

It’s terrifying.

And exhilarating.

When you think about it, a lot of that 90% is probably the grind (and not fun) anyway.

It’s the stuff that drains you. The tasks you do on autopilot.

Losing that part might be good news.

So what should you do?

There’s a lot of pressure right now to use AI.

On everything. As fast as possible.

Like AI fairy dust, you sprinkle on your problems and hope for the best.

But the smartest move is going back to basics first.

I know… not super sexy, but stick with me.

Try this

Grab a piece of paper and map one process.

Something simple, like how a new connection finds you on LinkedIn:

1. They see a post

2. They click your profile and connect

3. You reply and a conversation starts

4. You track them in your CRM

5. They opt in to your newsletter

6. You share frameworks, tools, ideas - at scale or one to one

See what’s actually there. Then figure out what each step needs:

• The reply: You or an assistant. Human. Always. (LinkedIn doesn’t like external plug-ins, plus this is the best part and opportunity. Connecting with new people.)

• The CRM tracking: Automation possibilities

• The newsletter: A content system to capture and send.

• The frameworks and tools: your 10%.

Then the biggest questions of all

If you offload the 90%... what do you do with that time?

Do you do more? Or do you do less?

Do something different?

And what’s that 10% that’s your super power? The one you can 1000x?

As I said, I can’t stop thinking about this and am still working through mine.

Do you know yours? Maybe you know both.

Either way, start brainstorming and let’s keep the discussion going.

✈️ Carry On
with Pamela Wilton

Stay in touch, stay visible, stay helpful.

Increase your luck surface area.

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If you had told a 22-year-old me that sales would be a big part of my career, I would have politely nodded, smiled, and said, “No chance.”

(In a nice way, of course. On brand.)

I used to think sales meant being pushy. Cringy tactics.

Having a “used car salesman” era.

Then I spent 15 years in aviation, and I learned something quite different.

One deal. Three conversations.

Several years into my airplane career, I was working on selling an engine to a lessor. Eight months, start to finish.

These deals are intense. Lots of moving parts:

• The technical team wanted specs. Precise, detailed, no fluff.

• The contracts and finance team wanted compliance and numbers.

• Leadership just wanted to know it was getting done.

Same deal. Three completely different conversations.

And somewhere in those eight months, I realized selling is not cringy. At all.

What this means, even if you’re not in aviation

In reality, business development is about education.

Marketing educates at scale. Sales educates one-to-one.

Your job isn’t to convince anyone. It’s to help them understand their challenges, the opportunities they’re missing, what’s possible.

When you show up that way, consistently, you become a partner. You form a professional relationship. You solve problems and grow your business.

That’s what I help my clients build today. Create systems to share their expertise on scale and one-on-one. Capture leads, answer questions, nurture the best relationships.

All while they keep doing what they do best.

✈️ Carry On
with Pamela Wilton

Stay in touch, stay visible, stay helpful.
Increase your luck surface area.

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I was catching up with a fellow entrepreneur this week.

She has a great referral network, a similar business to mine, different niche. She’s been showing up more lately … events, posting regularly on LinkedIn, and sharing a weekly newsletter with her audience.

Doing a fab job, honestly.

But something was holding her back on outreach.

“It feels different to reach out when there’s a business purpose to it,” she said.

I get that.

But also, it doesn’t have to feel that different from a typical professional catch-up.

So I shared a few things that have worked for me.

Let’s do some business math.

You connect with one person per week. That’s 52 new contacts in a year.

Each person in your network has about 200 connections of their own.

So one coffee chat today could lead to collaboration six months from now. Or a referral you didn’t see coming. Or just the positive feeling of reaching out.

Most people know they should stay in touch. They just freeze when it comes to actually doing it.

The guilt. The “it’s been too long.” The fear of being pushy.

Or gasp! Salesy.

Here’s what I’ve found after years of building relationships across the globe. You don’t need grand gestures. Just small, consistent touchpoints.

Here’s how to make staying in touch work without feeling annoying or overwhelming.

Start with a focused list

I’m one of those “the world is my oyster” kind of people.

In the past, I’d meet someone amazing and add them to this large list of people I “should” reach out to.

That list grew. My follow-through didn’t.

Now I keep a focused list. 10-20 people I genuinely want to stay connected with over the next few months.

This makes it manageable. And you’ll actually do it.

The “I was thinking about you” check-in

This is my favourite. Just a genuine check-in.

“Hey, I saw your post about [topic] and it made me think of you. Hope things are going well.”

Or even simpler: “Hope your Q1 is going well!”

And mean it.

These messages take 30 seconds to send. They’re low-friction for both of you. And they keep the connection warm.

Comment on their LinkedIn post

You see someone’s post. You read it and you think, “Good point.”

Take one extra step and leave a comment.

And not a generic “Great post!”

Something thoughtful like a question or a quick story of your own.

This keeps you visible and shows you’re paying attention. Helpful, not pushy.

Forward a relevant article

You read something and immediately think, “This would be perfect for [name].”

Send it. Right then.

“Saw this and thought of you. Hope it’s useful.”

These small gestures matter. They show you’re thinking about them even when you’re not asking for anything.

The no-agenda coffee

Book a call or grab coffee with no agenda. Especially if you have met before and there were good vibes, but you haven’t officially collaborated yet.

I did this a few months ago with a friend.

Logistically, it was a challenge. But we finally made it happen.

What started as a casual chat turned into a new business opportunity and a deeper connection.

You can’t predict what will come from these conversations. But they do compound over time.

Send a quick voice memo or text

Email feels formal sometimes. A voice memo or text can feel more personal.

“Hey, just wanted to check in. How’s [project/trip/event] going?”

Quick and easy to respond to.

I’ve been playing with Loom since I started my business, and it’s been a fun way to connect. Worth experimenting with!

Stay visible with strategic updates

You don’t have to reach out to everyone individually all the time. That’s not realistic.

My updates look like this: a weekly newsletter, regular LinkedIn posts, Substack notes.

Your own version of this will keep you top of mind without requiring anything from the other person.

They can engage when they’re ready. Or they can just follow along.

Either way, you’re staying visible and helpful.

The magic is in the consistency, not the size of the gesture.

You just need to show up.

Regularly. In small, helpful ways.

That’s how you grow your luck surface area.

The opportunities will compound.

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.
Expand your luck surface area.

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Your best content is sitting on your website.

Case studies. Frameworks. Industry insights. The stuff your prospects would actually love to read.

And (unfortunately) nobody’s finding it.

Last week, I talked with a client who’d spent months creating an incredible destination guide. Beautiful design, useful information… but buried on their website.

Their sales team was sending cold emails asking for meetings. Their marketing team was building more pages. Both working hard, neither helping the other.

Sound familiar?

Misaligned sales and marketing costs B2B companies about 10% in revenue every year. When they align, that growth jumps 32%.

Even if you’re a team of one, this applies to you.

Here’s how to turn that buried content into something that actually works.

Build a lead magnet that travels

A lead magnet is your best content, packaged in a way people actually want it.

Here’s what makes one work:

• It solves a specific problem. Not “everything about our industry.” More like “how to solve this one thing.”

• It delivers a quick win. People finish it feeling smarter, not overwhelmed.

• It invites the next step. Book a call, reply with a question, keep the conversation going.

A simple mini course works incredibly well. Take your best content, break it into five digestible emails, one insight per day.

Same content. Multiple uses.

Use it to capture emails at scale.

Someone downloads it, opts in, gets the course automatically. Educating prospects without lifting a finger.

Use it for 1:1 outreach.

When there’s a specific prospect with a specific problem, share the relevant piece directly. Personalized and tied to exactly what they need.

85% of professionals say sales-marketing alignment is the biggest opportunity for improving business performance.

This is how you make it happen.

Take your best website content, turn it into something digestible. Help those who want to work with you find you.

Then work happily ever after. Together.

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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Imagine someone walks up to you at a conference and introduces themselves.

You smile, nod, and then… walk away without saying a word.

Weird, right?

Of course, that would never happen in person.

But online, it happens all the time.

Someone joins your email list, signs up for your newsletter, or connects with you on LinkedIn.

They’re interested in you. Maybe they want to buy, sell, collaborate, or just think you look really cool. (Obviously, it’s the last option at minimum.)

And the typical response is… nothing.

With emails, there might be a template response. Heavily branded by the email platform, not you. With social media, there’s no response at all.

Welcome messages get 4-5x higher open rates than regular emails. People are paying attention right now. A little effort here goes a long way.

Here’s where to start.

• Substack. Growing in popularity, the platform lets you craft a welcome email. You can thank subscribers for joining, set expectations, and give them something useful right away. (Are you on Substack yet? If so, we should connect!)

• Kit or your email platform. There are more options, like building a short sequence. A few emails that build trust and share your best stuff before you ever ask for anything. Set it up once. It runs forever.

• LinkedIn. The biggest opportunity for everyone, especially if you’re growing a business or a network. When someone connects, send a short message. Reference something from their profile, ask a genuine question, or just say “hello”. Some powerusers see the value in this and have hired a VA to help with initial welcomes. Then they take over if the conversation keeps going.

And I’ll be honest - I’ve been dropping the ball on the DMs lately. As I’ve continued to post daily on LinkedIn and engage in comments, I’ve missed my 1-1 conversations.

Writing this is a reminder for me, too.

That initial connection point is low-hanging fruit. Loads of upside.

The “welcome moment” is right there.

Worth making the most of it.

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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Last year at Web Summit Vancouver, I tried something new.

I interviewed fifteen people. It involved four rapid-fire questions and a request to wave at my camera.

(Yes, I was levelling up my video game! More on that soon.)

Here’s what I asked:

1. What’s your favourite travel hack?

2. What’s your favourite event hack?

3. Carry-on or checked bag?

4. Are you pro-bleisure? Or not?

The responses were gold.

One stat jumped out: 100% said they were into bleisure.

(Bleisure is business and leisure travel. Extending that work trip with some personal time to explore the destination.)

Full transparency: 75% were actively bleisuring at that very moment. So, the sample was high on quality, light on quantity.

But still. The point stands and you know I’m here for it.

Business travellers today want more from their trips. They’re extending stays, exploring cities, mixing work with life in ways that make the whole experience better.

Here’s what else they shared.

Travel hacks:

• Use a VPN to find cheaper international flights. Switch your location, compare prices, save money.

• Book the aisle + window seats and hope for an empty middle. Risky, but when it works? Chef’s kiss.

• Use packing cubes. Game-changer for carry-on organization.

• Add an AirTag to your checked bag. Peace of mind when your luggage decides to take a detour. (Although some airlines like Air Canada have a great tracking system.)

• Have a repeatable, layered flight outfit ready. Comfort plus adaptability for different climates.

Event hacks:

• Wear sneakers, no matter the outfit. Your feet will thank you by day two.

• Research speakers and attendees in advance. Know who you want to meet before you arrive.

• Bring snacks. Being hangry kills connection. I always keep a protein bar in my bag.

• Schedule your top sessions in advance. Build your agenda early. Don’t wing it.

• Sit with new people at every session. Maximize serendipity, skip the comfort zone.

Honestly, I appreciated every single one of these. Many are already part of my travel routine. Others felt fresh or were ideas I’d completely forgotten about.

Plus, a fun new video experiment in the books!

If interested in the video preview, here’s a fun LinkedIn post I did about it.

And now I’m curious… what’s your go-to travel or event hack?

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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I went to Ethiopia twice in six months for two different aviation conferences.

Different events, but a lot of the same people. Same venue. Both rich with opportunities.

The first trip, I did what most do.

Set up my booth, exchanged business cards with people I’d never met before, and attended sessions. I managed one partner dinner. Made some solid initial introductions and flew home feeling good about it.

Then the real work began.

I followed up with the people I’d met and stayed in touch over the next several months. I reached out on LinkedIn and sent emails with helpful information. Even set up a few calls to keep the conversation going.

When I headed to Ethiopia for the second time, the experience was completely different.

It started with my flight over, when I discovered I knew most of the people in business class. Updated a client in the lobby while checking in. I had pre-arranged site tours, sit-down meetings with a group of buyers from a major airline, and more dinners.

The power of staying in touch.

I shared a stat recently that said 80% of exhibitors don’t follow up on their leads at all. They spend thousands on booth space, fly across the world, have great conversations, and then get home and... nothing happens.

The real ROI happens in between events.

Here’s what actually works:

• Segment your leads. Hot leads (meeting booked, proposal requested) get a personal note within 24-48 hours. Warmer leads who opted into your lead magnet are added to a nurture sequence. Colder leads will need multiple touchpoints.

• Use multiple channels. Email, LinkedIn, phone calls. Maybe a handwritten note for your best prospects. Stay visible without being pushy.

• Share real value over time. This is where a strong lead magnet pays off. Organize your email list to deliver ongoing case studies, insights, and tools through an email sequence. Repurpose it for follow-up emails and social posts. Give prospects reasons to stay engaged.

You don’t need a huge team. Just a plan and the commitment to execute it.

Keep it simple and send that thank-you email within 48 hours. Build a system that keeps relationships warm until the next event. Track, reach out, repeat.

Because return on relationships takes time.

The event is just the starting point.

The magic happens in all those months in between.

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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It’s Friday afternoon, and I’m hanging out in a local tech company’s kitchen. The Olympic opening ceremony is playing in the background.

I’m across the table from the founder and his COO, and they share a story that probably sounds familiar.

They launched their business with a flagship client and an amazing referral network.

In fact, they’d done such a good job that their well was starting to dry up.

They need to meet new people. It’s time to make new friends.

Their next move is to attend a large industry event in Las Vegas.

But they’re not salespeople. (Their words, not mine.) They’re uncomfortable putting themselves out there.

Of course, they’re not alone. On top of “not feeling salesy”, so many businesses spend thousands on these events. They show up, network, and then nothing happens. (Yikes).

The business cards go in a drawer, and opportunities are lost.

It needn’t be that way.

When you meet someone amazing at an event, this is what you do:

Level 1: Book them for a meeting right there on the spot. Pull out your phone. “Let’s have a virtual coffee in two weeks. What does your Tuesday look like?”

Level 2: If they (or you) are not ready for that, offer something valuable immediately. A QR code to download a resource. An email opt-in for instant information and ongoing nurturing.

Level 3: Connect on LinkedIn.

Level 4: Grab the business card.

The long-term play is attending the same events multiple times. The touchpoints become warmer and the dinner dates grow. But only if you keep the connection alive in between.

Otherwise, your existing circle might continue to feed your business for a while. And people might find you.

But what if they don’t?

Make those business events count.

And now… I’m curious.

What’s your move when you meet someone interesting at an event?

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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If you post on LinkedIn, you already know the feeling.

Some do well. Some fall flat. And it can be hard to tell what’s actually working.

​

On a Sunday morning a few months ago, I’m on my second cup of coffee, laptop open.

Pax is giving me literal puppy dog eyes. It’s dog park time.

I’d been thinking all week about a funny video about “Email Meeting.” On brand, relevant, kind of silly.

Wrote some copy, hit post. Pax and I head to the park.

​

A few weeks later, I was surprised to see some likes and comments for “Email Meeting”.

Then, it didn’t STOP getting traction.

Two months later, 274,155 impressions.

(Viral on LinkedIn is over 50K-100K.)

I still get notifications on it every day.

The results are in:

It’s a fun achievement. There are a few more follows and profile views.

Life continues.

​

It’s true about the algorithm lottery.

What I’ve learned is that it remains a consistency game.

Keep sharing valuable and relevant content.

You’ll ultimately see positive results and opportunities, whether the numbers support it or not.

​If you’re curious, check out “Email Meeting” here. ​

If nothing else, it’ll make you smile or scratch your head.

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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I’ve been posting on LinkedIn every day since January 2025.

Over 365 days straight.

And in 2026, I added daily Substack notes to the mix.

You might be thinking:

“That sounds exhausting.” Or “I don’t have time for that.” Or “What would I even post about?”

Yeah. That was me too.

When I started, I had no clue what my voice was. What my content pillars should be. What you actually wanted to read about.

I was building a new business. Traveling. Showing up at events. Touring with an ultimate frisbee team for the first time. (Yes, really.)

Some days I stared at a blank screen thinking, “I have nothing to say.”

But I posted anyway.

Here’s what actually happened:

Inbound clients started showing up. They’d been following along and already knew what I was about.

My writing got faster. Clearer. More like me.

And the connections… Some of you I’ve met in real life now. Others, one day soon.

The thing I didn’t expect (but hoped for):

The more I showed up, the luckier I got.

Increased my luck surface area.

When you show up consistently - sharing what you’re learning, what you’re noticing, what you’re working on - opportunities find you.

People reach out. Ideas connect. Doors open that you didn’t even know existed.

So here’s my question for you:

What’s one way you could increase YOUR luck surface area in 2026?

Daily posts? A weekly newsletter? Finally showing up at that event? Sharing more of your work in progress?

You don’t need to figure it all out first. You just need to start.

✈️ Carry On
with Pamela Wilton

Stay in touch. Stay visible. Stay helpful. Have fun.

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