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Hey Reader,

In the past year, I’ve heard some variation of “selling feels harder” so often that it deserves its own entry in the Strategic AF glossary.

My clients and my friends say it after they’ve done aaalll the “right things.” They’ve posted consistently. They’ve improved their copy. They’ve refined their offer. They’ve tried a launch. They’ve tried soft selling. They’ve even tried being annoyingly visible, just to see if shame and volume would do the trick.

Then they look at the results and think: maybe I lost it.

If that sounds like you too, the first thing you need to know is that you didn’t lose it. You’re just selling inside a different environment and likely using an outdated playbook.

We all feel it. I feel it too, and it’s uncomfortable AF.

So I started digging because I believe that understanding the constraints helps you design a growth system around them.

TL;DR: selling feels harder because the path between “I’m interested” and “I’m buying” got longer, and the systems we rely on to bridge that gap got noisier, less stable, and less generous.

We’ll unpack that in a second, after a quick message from today’s partner, a fairly recent discovery of mine that you absolutely need to know about.

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What’s happening isn’t just a marketing problem anymore. It’s a decision-making problem, shaped by forces that sit outside any one platform or tactic.

You might feel the pressure at the point of selling, but the causes show up much earlier in the process.

1. People are deferring decisions, not rejecting them

One of the biggest shifts is temporal. Across industries, buyers are taking longer to decide.

This always happens when the environment is uncertain because people need to optimize for reversibility. They want to minimize risk and regret, so even if the interest is there, they will delay the decision for as long as possible and seek additional reassurance before committing.

For solopreneurs, this shows up as:

• Longer gaps between engagement and purchase
• More “I’ll come back to this”
• Fewer impulse buys, even at lower price points

Selling feels harder when you interpret delay as disinterest. The good news is that, in reality, delay has become the default.

2. Cognitive load is eating the margins of persuasion

Marketing 101 says you should design for busy people, especially in B2B. That's still true but with an added layer: your buyers are busy AF AND cognitively saturated.

​Research in behavioral science consistently shows that decision quality degrades under high cognitive load. When people are juggling too many inputs, they default to status quo choices and postpone discretionary decisions.

This matters because buying from you is rarely urgent. It’s optional. Optional decisions are the first to get postponed when mental bandwidth is scarce.

Selling feels harder when you’re competing with exhaustion, and, if you look at what’s happening in the world right now, you’ll understand why everyone is exhausted.

3. Trust thresholds have moved upward

Trust has always been required for selling. What changed is the amount of trust needed to act.

​The Edelman Trust Barometer shows a continued rise in scepticism toward claims, expertise, and authority, paired with a stronger demand for demonstrated competence and consistency.

In practice, this means:

• People need more exposure before they feel safe buying
• ​Social proof alone carries less weight
• ​Credibility is assessed over time

“I’ve been reading your newsletter for a while, and now I’m interested in [product/service name]” is how many of my client conversations start these days.

If I check their profile, it’s months, or even over a year, until they’re ready to buy something over $100. My smart clients know that anyone can fake 1-2 trust-inducing pieces of content, so they wait.

They wait until they know for sure that I’m someone who can help them.

And, because attention is a loop, not a funnel, there’s rarely a straight line from discovery to purchase.

One other thing I’ve noticed recently is that I get a lot more questions about my products and services before a purchase. This is especially true for new buyers, for people who have only interacted with my free content.

They get very specific before they buy. I get questions I never got before:

• What’s happening in The Council? Is there async support if I can’t make the live calls (yes, there is)? Are there people like me in there?
• If I buy a strategy session, can you help me with this specific problem? Have you helped anyone with it before?
• Does the Newsletter Growth Bootcamp come with Q&As (it does)? Will you address my specific challenge (yep)?

I usually take these questions as an opportunity to update my assets and address questions/objections on landing pages. However, it’s very interesting to see how the buying behavior has shifted — and not always to the seller’s advantage.

4. Value is being evaluated relative to alternatives

These days, people compare offers against opportunity cost more than against your positioning.

They ask:

• “What would I not do if I said yes?”
• “What else could I spend time or money on?”
• “Can this wait?”

This is especially true for solopreneur audiences, where time is often scarcer than money.

As choice sets expand, people become more conservative and selective. Selling feels harder when your offer has to justify itself against everything else competing for attention, not just similar products.

As I like to say, you’re competing with every cat video, news cycle, and email out there, not just with your direct competitors.

5. AI — yep, I’m going there

Like me, I’m sure you’ve thought of the ways AI can replace you. And, whether we like it or not, it’s happening.

People are even outsourcing their physical and mental health to AI, so everything else — from business coaching to strategy feels like a small risk with a high potential pay-off.

Like you, I know that AI can’t be a good strategist because of the way it’s built. Just like it can’t replace your coaching, your advice, your depth of knowledge.

The sad truth is that all of the above matters less than what our clients believe. AI is faster and cheaper than anything a human can sell, so people will try it before realizing it’s not what they need. Worse yet, they often won’t realize AI isn’t good enough.

The solution, you ask? Candidly, I don’t have a foolproof one.

What I do know is that it’s important to stick around long enough for people to realize they need your help and challenge their use of AI through your own results.

One thing I found useful is coming up with solutions that are inherently built as resistance to AI. This is why I’m so proud of The Council, for instance. I look at our feed in there, and I see a monumental difference between it and the AI slop on social media.

People ask real, vulnerable questions and offer good advice. They post resources they use themselves instead of half-assed rags-to-riches stories.

This is the kind of shelter from the noise we all need these days. My challenge to you is “what kind of space that feels like a shelter makes sense for your business?”

It doesn’t need to be a community; it can be any other container that stops the noise and promotes real transformation.

So what do you do with this?

You can’t outwork structural shifts. This is why I had to include the AI bit above.

You can, however, design around them.

The goal becomes simple (simple is not easy!): increase the number of qualified people who stay close long enough to buy later, and reduce dependence on channels that reset you every day.

I recently spoke about how only a small percentage of your audience buys from you – and why that’s normal.

Let’s see how you can increase that percentage, along with increasing your audience.

Build one “top-of-mind” channel you control

Email newsletters work well for a boring reason: repeated contact without algorithmic gatekeeping.

You can show up consistently in a predictable environment. That predictability reduces cognitive load and builds recognition.

Your audience doesn’t need to read every email. They need to remember you exist, understand what you stand for, and associate you with a specific problem you solve.

Social platforms can still drive discovery but the feed rarely sustains closeness.

More about this and about how to choose between push and pull marketing here.

Design for delayed decisions on purpose

Assume most buyers will need:

• Repeated exposure
• Multiple angles
• The right moment/trigger to buy

Then build a system that supports that reality:

• A welcome sequence that sets expectations and direction
• A simple “here’s where to start” path
• Periodic re-entry points for lurkers
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Do outreach BEFORE you need it

Because sales cycles are longer, you can no longer afford to start prospecting when your pipeline is empty. With inbound getting harder, your outbound strategy needs to be a constant, not something you do when you finish working with the last client.

So:

• Block time for outreach every day/week
• If you’re a service provider, book your clients months in advance. Build a waitlist if you need to.
• If you sell digital products, keep prospecting and growing your audience even after you’ve hit your monthly target. Remember, there’s a seasonality to every business, so buffers help — next quarter may not look as good as this one.

This is one of the first lessons I learned when I first started out as a freelancer. I was working on freelancing sites (1/10, I don’t recommend) and I was ABP-ing (Always Be Prospecting) the hell out of it.

No matter how big my to-do list and client roster were, I always started my day by bidding on new projects on those platforms. That was my one non-negotiable, and it paid off — after the first 3 months, I never had a feast-and-famine cycle again.

Borrow other people’s trust and distribution

When platforms get stingier, relationships get more valuable.

Partnerships, podcast guesting, newsletter swaps, co-created assets, guest trainings. Done well, these compress trust and reduce the cost of attention.

Done badly, they become empty audience trades.

We’ll cover this extensively in the Newsletter Growth Bootcamp, BTW!

Invest in retention and expansion

Selling feels harder when every month starts at zero.

A stronger base makes the environment feel less hostile:

• Renewal loops
• Upsells that solve the next problem
• Referral prompts that feel natural
• Community touchpoints that create stickiness

This is the least sexy lever, which is why it also tends to be the most profitable.

This is a good primer on retention.

All of this is exactly why I’m running a Newsletter Growth Bootcamp

A newsletter done well functions as infrastructure: it keeps the right people close, builds memory, and makes selling feel less like starting over every week.

Inside the bootcamp, we’ll work on the pieces that move the needle in this environment:

• The promise and positioning (why subscribe, why now)
• Acquisition paths that don’t rely on algorithm luck
• Landing page friction and conversion leaks
• Cadence and content design that builds recognition
• Teardowns to diagnose what’s breaking your loop

This is all VERY hands-on. 90% implementation and 10% theory. Join us!

The Council Bulletin

As we get ready to kickstart the Newsletter Growth Bootcamp, The Council welcomed a few bootcampers and one new full member in the past week.

We’re now over a month in, and I’m increasingly happy with how the community is shaping up. Council members are settling into a rhythm and I can see that some members are already thinking about it as the first place to come to when they face a challenge.

If you need a shelter from the AI slop on social media, join us!

One last thought

I struggled with this piece a lot, far more than usual, because I realized I don’t have one solution that fits every sales challenge across every vertical. Ultimately, I decided to write and publish it because I want you to know that, if selling feels harder, you’re not alone.

We’re all in the same boat.

One thing I do know, though, is that you’ll figure it out. The key is not giving up — not on your business as a whole and not on what you’re selling right now.

Give it time. It always takes longer than we think.

If you feel I can help, drop me a line. Reply to this email with your current challenge and I’ll reply back with a solution.

That's it from me today! See you next week in your inbox. Here to make you think, Adriana

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