When it comes to rail tricks, we all begin with learning how to get into rail stand. Tailstop to heelside rail is easy-peasy; most new freestyle skateboarders get the hang of this within a sesh. Cleanly pulling up into heelside rail requires more skill, although, once mastered, it can be a safe and consistent method. And then there’s the dreaded toeside-rail entry. 😭
In terms of difficulty, toeside-rail entry ranks higher than tailstop to heelside rail but lower than pulling up into heelside rail. It requires less prerequisites. If you can hippie jump, if you’ve got decent balance and proprioception, then you can make the trick; you just need to be gutsy.
So how do you find the courage to hop into toeside rail?
Uncertainty is what we’re really afraid of
It’s normal to be wary of a new trick. Will it be a make? Or will you misjudge and end up with a wheel-shaped bruise on your butt? Or worse, a twisted ankle?
In a BBC article about the fear of the unknown, science writer David Robson wrote that a ‘feeling of uncertainty can bring acute discomfort’. Some rather horrible studies involving participants being zapped showed that having a fifty percent chance of receiving an electric shock was more stressful than being guaranteed a shock.
He noted that such a response has an evolutionary benefit.
The brain is constantly trying to predict what will happen next, allowing it to prepare the body and mind in the most effective way possible. In uncertain situations, that planning is a lot harder – and if you’re potentially facing a predator or a human foe, the wrong response could be deadly. As a result, it could pay to err on the side of caution – either by avoiding the uncertainty altogether or by putting the brain and body in an aroused state that is ready to respond to a changing situation.
Danger and uncertainty is skateboarding. That adrenaline rush we get is why we fell in love with the sport in the first place. But too much fear can cause frustration and delay progress. So how do we skateboarders circumvent the anxiety when it gets too much?
Exposure therapy is key
Clinicians use behavioural therapy to help patients with phobias. One evidence-based approach is exposure therapy where patients are encouraged to face their fears.
According to the Australian Psychological Society, the best method is ‘typically conducted in a controlled real-world environment and involves directly confronting the person’s fear through a series of activities which provoke increasing levels of fear and anxiety’.
This step-by-step process is known as ‘graded therapy’. You start with the easiest, least anxiety-inducing exposures, working up to harder ones later on.
In relation to toeside-rail entries, you might start by setting the board into toeside rail and then jumping up onto it. This removes the uncertainty of the board over or under-rotating and you can just work on getting comfortable with the landing.
The next step would be holding onto a rail, fence, or a skate buddy with two hands while attempting the trick. Once comfortable, try doing it with only a one-handed assist. Then, attempt some without holding onto something, but with the fence or rail or skate buddy nearby, so that you can grab onto them should things go pear-shaped. With enough work, you will be able to graduate to an unassisted toeside-rail entry.
The Western Australian Government’s Centre for Clinical Interventions (CCI) has various self-help resources on anxiety, including ‘Situational Exposure’, an excellent two-pager which helps people plan their own graded-exposure therapy. It’s worth checking out if you’re a nervy skateboarder.
The American Psychological Association also uses ‘flooding’ as a type of exposure therapy. The opposite of graded therapy, flooding requires you to address the hardest, scariest, most difficult situation first.
If you are nervous about toeside-rail entry, you might want to work on something more intimidating, like trying it rolling, trying it one-footed or trying it in front of a bunch of unimpressed bystanders. You don’t need to commit and you don’t need to be unsafe; it’s more about testing out something that absolutely terrifies you and then returning to the relatively easy trick of getting into toeside rail on your favourite bit of flatground.
Also, the hardest, scariest thing that beginner freestylers can imagine is failing. So practise failing! Deliberately under-rotate the board and learn how to slap it back down to bolts so that it no longer freaks you out.
I didn’t sign up for the science talk…how do I learn to love toeside-rail entries?
This post turned out to be less skateboarding and more medically minded. I should make a proviso: I’m not a psychologist, but rather just a chicken-hearted freestyle skateboarder who is coming to terms with mildly intimidating tricks.
To summarise the above, create a controlled environment by
- removing the uncertainty of an over-rotated/under-rotated board by placing the board in toeside rail before practising jumps, and
- using a safety net like a fence, rail or skate buddy.
Use a step-by-step approach (aka ‘graded exposure’) by
- trying with a two-handed assist
- trying with a one-handed assist, and
- trying without assistance but with the safety net (i.e. fence, rail, skate buddy) nearby.
Alternatively, do the scariest thing first (aka ‘flooding’) by confronting scarier situations like
- failing/falling, and
- one-legged toeside rail entries.
A final note
If you’ve done any kind of skateboarding for a time, you’ll know that progress is rarely linear. Overcoming the anxiety isn’t linear either but, just remember, if you keep at it, doing the trick will one day become second nature and that stress will morph into the best kind of dopamine. In the meantime, put your headphones in, turn the chill music on, and face that fear.
REFERENCES
- American Psychological Association (2017), What is exposure therapy?, apa.org, accessed 23 September 2025
- Australian Psychological Society (n.d.), Phobias, psychology.org.au, accessed 24 September 2025
- Centre for Clinical Interventions (n.d.), Situational Exposure, cci.health.wa.gov.au, accessed 24 September 2025
- Robson D (2021), Why we’re so terrified of the unknown, BBC, accessed 23 September 2025