How can I overcome feeling scared of September?

The ‘new term, fresh start’ used to be exciting, but now it feels intimidating – how can I handle the creeping dread?

I’m a 45-year-old, recently self-employed woman and I always used to really look forward to September. I was all “new term, fresh start” and it felt like an opportunity. But I’ve noticed in recent years that I start to dread September from around mid-July. Where it used to feel exciting, it now feels frightening and intimidating – as though I won’t be able to step up and handle life. It’s almost ruining my summers. Why do I feel like this and how can I handle the creeping dread?
– Septemberphobe
What we are experiencing right now is what’s known as a hard relate. When did September mutate from a shimmering sea of possibility into a quagmire of murk? When did opportunity morph into threat? How did our summers become polluted with – as you say – creeping dread. A joyfully hopeful “Anything could happen” metamorphosed into a shrilly panicking “ANYTHING COULD HAPPEN!”
And, yes, it starts in July. When we are tired and vulnerable, many of us looking forward, with a sort of muted hysteria, to long-planned, slightly unaffordable holidays which we pray will “cure” us. We’re not meant to feel weird in July. We’re meant to feel optimistic in July. We’re practically ordered to feel brilliant in July. But July is the waiting room of summer – and waiting rooms are weird: you don’t know if they are going to change your life for the good, for the bad. And then we enter the odd, muted month of August. Long and short at the same time. Both flying past and somehow operating in slow-mo. 
July, August and September all mash up into one f–ked-up summer “quarter” when we have to think about all three months at the same time. All the thinking. The pre-holiday double workload. The holiday stuff… and there is so much holiday stuff, from money panic to unknown, untested destination panic, to packing panic, to more (much more) money panic.
And the September planning. 
And we don’t plan small, so we? Oh no, we plan big, heaven help us. You say in your letter that you fear your own inadequacy in terms of “stepping-up”. That’s a huge ask. Almost an act of self-loathing or, at least, self-sabotage. How can I be what I was always meant to be in September? How can I meaningfully improve in terms of performance/creativity/organisation/charisma/earning power/the list goes on and on… This is Sunday night dread on steroids, amplified to the point of distortion and paralysis. No wonder it’s slightly ruining your summers. Nothing feels simple…
And we are talking about mid-life September. Not only that but mid-life, freelance September (scream emoji) in a world of speedily shifting sands. That sparkly September feeling of old was, perhaps, in some way emblematic of the feeling that you had your whole life ahead of you. These days, your whole life is not ahead of you but there is a lot of time left to howl “What the hell am I going to do?” into the void. And, by the void, we mean September. That old September optimism existed in a strict and supported framework of employment with a broadly anticipated trajectory. As a recently converted freelancer, you are experiencing a fresh flavour of stress. You are no longer run by anyone else but neither are you an employer’s responsibility, and so you must find the rocket fuel to drive yourself forwards into so many unknowns. Will anyone care? Do I even care? I do care but I’m also a bit tired and can I lie down?
Here’s some advice that we, ourselves, are attempting to put into practice: think small around big feelings. Deciding that September is the season of infinite possibility is really alarming and raises your expectations of yourself to a deeply unnerving degree. Rather than looking forward to some kind of limitless concept of success, it might be more helpful to look forward to pockets of joy. Small things that deliver for you. A swim. A diary. A gym class. Look forward to feeling good and productive rather than the end result. The end result is large and road-mapping is hard. 
Create small monthly goals – North stars, if you like – and check-in on those, maybe with a trusted friend or even a coach. Without a manageable framework, it is as though you are saying to yourself, “I’m going to get incredibly fit in September” while being too intimidated to start exercising. Start with five minutes. It won’t have you running a marathon by the end of the month but it will take you closer to “success” than sitting in a chair, eating toast and feeling frightened. 
Small, methodical chunks of time dedicated towards things that matter to you are much more likely to deliver and will go some way towards neutralising that bastard, creeping dread. September is just September. Imagine it naked and sitting on the loo. Phobes are phobic because they are afraid. September can’t hurt you but your feelings around it can.
You’re the boss now. Lay down the law.
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