Why Learning a New Trick and Launching a New Store Feel Exactly the Same

By Trevor Fenner | Updated 2026

I’ve been skating since I was a kid in Seattle and building businesses since I was in my twenties in Los Angeles. For most of that time I thought of them as completely separate pursuits: one was how I stayed sane and connected to something physical and creative, the other was how I paid for my life.

It took me longer than it should have to notice that the internal experience of learning a new trick and launching a new store are almost identical. Not similar. Identical. The same sequence of emotions, the same psychological obstacles, the same patterns of progress and regression, the same moment of breakthrough that feels like it comes out of nowhere after a long stretch of nothing working.

Once I saw it I couldn’t unsee it. And understanding that parallel has genuinely changed how I approach both.

The Initial Excitement That Precedes the Reality Check

When you first decide you’re going to learn a new trick, there’s a window of pure optimism. You’ve seen the trick done. You understand conceptually what needs to happen. You can picture yourself doing it. Everything feels possible before you’ve actually attempted it and discovered the gap between understanding something and being able to do it.

Launching a new store has exactly the same opening act. The niche research phase, when you’re identifying the opportunity, mapping out the supplier landscape, and imagining what the store could become, carries that same quality of pure potential. Everything looks achievable on a spreadsheet before the reality of building it introduces all the complications that weren’t visible from the outside.

That initial excitement is not a problem. It’s useful fuel. The issue is when people confuse the excitement of the idea phase with actual progress. Visualizing a trick and watching footage of it is not the same as attempting it. Building a niche research document and a business plan is not the same as building the store. The excitement is the starting point, not the destination.

The First Attempts Are Always Humbling

The first real attempts at a new trick are almost always worse than expected. Not because you’re doing something wrong, but because the gap between understanding a movement and having it in your muscle memory is enormous and can only be bridged by repetition. Your body does something completely different from what you intended. The board goes somewhere you didn’t plan. You feel less coordinated than you did before you started.

First attempts at a new store have the same quality. The first time you try to get supplier approvals, you discover that established brands have requirements you didn’t anticipate. The first time you run Google Ads on a new niche, the data looks nothing like the projections you made. The first product pages you write feel flat compared to the stores you were modeling. The gap between the plan and the execution is always wider than it looked from the research phase.

This is the stage where most people make the wrong assessment. They look at the gap between their first attempts and where they want to be, and they conclude that something is wrong with the approach or with them. Usually nothing is wrong. They’re just in the early attempt phase, which looks bad by design because it precedes the adjustment and improvement phase.

I see this constantly in students going through the Ecommerce Paradise masterclass. The first few weeks after launch, when the store is live but not yet performing the way they imagined, is when a lot of people start questioning whether they chose the right niche or the right model. In almost every case the answer is that they’re in the first-attempts phase, not the this-isn’t-working phase. Those are different things with different appropriate responses.

You Have to Identify the Specific Problem Before You Can Fix It

In skateboarding, progress on a new trick usually requires diagnosing exactly what’s going wrong. It’s almost never “everything.” It’s usually something specific: your foot position is slightly off, you’re bailing at the moment of commitment, your timing on the pop is a fraction too early or too late. Once you identify the specific problem you can fix it. Before you identify it you’re just falling without accumulating useful information.

Building a new store requires the same diagnostic discipline. When a store isn’t performing, “it’s not working” is not useful information. What specifically isn’t working? Is traffic not arriving? Is traffic arriving but not converting? Are people adding to cart but abandoning at checkout? Is the problem in the ad structure, the product page, the pricing, the supplier reliability, the niche selection? Each of these has a different fix, and applying the wrong fix wastes time and money.

This is one of the reasons one-on-one coaching produces results that self-directed learning alone often doesn’t. Having someone experienced look at exactly what’s happening and identify the specific problem is the equivalent of having a better skater watch your attempts and tell you precisely what to adjust. The diagnosis is often quick. The fix, once identified, is often straightforward. The obstacle was the inability to see clearly what was actually going wrong.

I use KWFinder for diagnosing SEO problems on stores because it surfaces exactly where the keyword targeting is off, which is one of the most common specific problems in new stores that aren’t getting organic traffic. Clean financial tracking through FreshBooks helps diagnose profitability problems specifically rather than just knowing generally that the numbers aren’t right.

There’s a Period of Apparent Stagnation Before the Breakthrough

In skateboarding there’s a well-known phenomenon among people who progress through difficult tricks: the session where it finally clicks rarely comes after a session where you were close. It often comes after a stretch of sessions where nothing was working and you were starting to wonder if you’d ever get it. The breakthrough appears to come out of nowhere.

It doesn’t actually come out of nowhere. The neurological and physical integration that makes a trick suddenly work is built up through all the unsuccessful attempts that preceded it. The brain and body are processing and adapting even when the visible results look flat. The stagnation is part of the process, not a sign that the process has stopped.

New ecommerce stores have an almost identical pattern. There is almost always a period, usually somewhere between weeks four and ten after launch, where progress looks flat. Traffic isn’t growing the way you expected. Conversions aren’t happening consistently. The ad campaigns are spending without producing proportional results. It feels like the store has stopped developing.

What’s usually happening during that period is the accumulation of data, supplier relationship development, search engine indexing, and campaign optimization that precedes real performance. The store is developing the way a trick is developing during the stagnation phase: not visibly, but really. The breakthrough, when it comes, feels sudden but it was built by everything that came before it.

Understanding this pattern is one of the most practically important things I try to convey through Ecommerce Paradise and through the community, because the stagnation phase is when most people quit. The stores that make it through that phase and into the breakthrough phase almost always become sustainable businesses. The ones that quit during the flat period never find out what was waiting on the other side.

The Mental Block Is Real and It’s Not a Character Flaw

Some tricks create mental blocks that have nothing to do with the physical difficulty of the trick. You might have the technical ability to land something but something in your brain is refusing to fully commit to the attempt. You pull back. You go through the motions without actually going for it. The block is real and it can persist for weeks or months regardless of your physical readiness.

Launching a store and building a business generate the same kind of mental blocks. Fear of investing money in ads that might not work. Fear of reaching out to suppliers and getting rejected. Fear of publishing content that might not be good enough. Fear of committing fully to a niche and being wrong about it. These blocks feel like practical caution but they often aren’t. They’re the business equivalent of pulling back on a trick you have the ability to land.

The way through a mental block in skating is almost always the same: you have to make the commitment decision separately from the execution. You decide, before you’re rolling, that you’re going for it regardless of what happens. Then you execute the decision you already made. The decision and the execution are two separate moments and the block usually lives in the gap between them.

In business the equivalent is making the commitment decision in advance and then executing it mechanically. You decide, before you open your email, that you’re going to send ten supplier outreach emails today. You decide, before you open your ad account, that you’re going to set the campaign live. You decide, before you open the content editor, that you’re going to publish what you’ve written. The decision is made. The execution is just following through.

I cover the full supplier outreach framework in my guide on how to find the best suppliers for high-ticket dropshipping, because supplier outreach is one of the most common places where the mental block shows up. The approach is straightforward. Most people know what they need to do. The obstacle is the block, not the lack of information.

Landing It Feels the Same Too

The first time you roll away clean from a trick you’ve been working on is one of the best feelings in skating. It’s not just relief. It’s the specific satisfaction of something that didn’t exist in your body becoming real through sustained effort. Nobody can take that from you. You did it. Your nervous system has it now.

The first real sale on a new store has the same quality. Not the first accidental click, not the first cart abandonment, but the first genuine sale from a customer who found the store, decided it was trustworthy, and made a purchase. It’s proof of concept in the most concrete possible form. Someone on the other side of the country, or the world, found what you built and decided to buy.

Both of these moments are the beginning, not the end. The trick needs to be landed consistently, in different conditions, before it’s really owned. The store needs to generate consistent sales, with reliable suppliers and a functioning ad structure, before it’s really a business. But both of those first moments carry the same specific feeling of something clicking into place that makes all the preceding attempts worth it.

That feeling is what keeps skaters coming back to difficult tricks and what keeps entrepreneurs building stores even when the early phases are grinding. It’s not irrational optimism. It’s the accurate memory of what it feels like when sustained effort finally produces the result you were working toward.

What I’d Tell a New Skater and a New Store Owner

The advice is almost identical for both.

Expect the first attempts to be worse than you imagined and don’t interpret that as a sign that something is wrong. Diagnose specific problems rather than concluding generally that it isn’t working. Stay consistent through the stagnation phase because that’s when the real development is happening even though it doesn’t look like it. Make the commitment decision in advance so the mental block doesn’t derail the execution. And understand that landing it once is the beginning of owning it, not the end of working for it.

If you’re in the early stages of building your first high-ticket dropshipping store and it feels like you’re eating concrete on every attempt, you’re in the right place doing the right things. Start with the free beginner’s guide if you’re still finding your footing. Get your niche selection right before you build. And get the legal and financial foundation in place from the start so you’re building on solid ground.

The trick is learnable. The store is buildable. The gap between where you are and where you want to be is bridged by the same thing in both cases: showing up, attempting, adjusting, and not quitting during the stagnation phase.

According to research from Stanford’s psychology department on the growth mindset, people who understand their abilities as developable through effort consistently outperform those who treat them as fixed traits, across domains from athletics to entrepreneurship. That research describes what every serious skater and every successful entrepreneur already knows from experience: the gap between where you start and where you can get to is real, and it’s crossed by the accumulation of attempts rather than by talent alone.

Keep going. The landing is in there somewhere.

Trevor Fenner is the founder of Ecommerce Paradise, an education and services platform for high-ticket dropshipping entrepreneurs. He has been building location-independent ecommerce businesses since 2013 and currently lives in Bali, Indonesia.