As will be evident to anybody who is familar with these pages, I’m quite a well-travelled girl. My work has taken me regularly to the United States, in particular, and to other destinations internationally – until Covid-19 changed everything. Meetings went online, and business travel, like so much else in life, became part of that different existence we led before the pandemic. In truth, while I enjoy travelling, I missed it much less than I might have expected during the pandemic. Perhaps because so much else in life changed it was less noticeable that I travelled less; I spent a lot more time at home and my social circle shrank. Moreover, while I do enjoy travelling, business travel is pretty hard work. Travelling en femme adds fun but also work – all those additional changes of clothing! Hauling bags down to Heathrow is a drag, and jetlag dents the week after one returns. There are trains, taxis, connecting flights…

For many years while I wrestled with my gender dysphoria and struggled to deal with its impact on my marriage, a week away from home on business also gave me opportunities to be myself; I regularly added a day or two of leave to a trip to allow myself a little “me time”, and this became an important source of solace, a chance to recover equilibrium and untangle some of the knots in my psyche, as well as providing adventures. But nowadays I step out regularly from home, and have much more liberty to be myself in Sheffield. Perhaps this also tipped the cost-benefit analysis of business travel more towards “cost” than “benefit”.

However, a couple of weeks ago I visited Chicago on business. As I booked my flight and hotel, I found myself increasingly excited by the prospect. I love visiting America, and Chicago has always been one of my favourite places; thus, while I had a packed programme of work ahead, I planned to sieze opportunities for a little pleasure while I was away, including a full day to myself at the start of my stay.

The excitement of travelling was returning, but as the day of my departure drew near, so, also, a less welcome apparition made a reappearance. If you’re familiar with my other posts, you’ll know that I have wrestled with what I call an “internalised transphobia”. That’s the best diagnosis I can manage, anyway. My best explanation is that after decades of attempting to cure myself, there is a part of me that still wants to point out the strangeness of a middle-aged man hauling a suitcase full of ladies clothes and make-up across the Atlantic. My sub-conscious generates “reasons” at quite a rate: it’s a busy week, and you don’t really have time; doesn’t all the organisation stress you out? Wouldn’t it be more relaxing to spend your time off with a novel? Haven’t you done this enough by now?

The “reasons” all feel compelling. Perhaps the last of those arguments was the most beguiling, because at some point while I was folding dresses and organising my suitcase I remember thinking to myself “maybe this is the last time”. Is it rational? Isn’t it actually exhausting – all the planning, the rushing back to the hotel to get changed in the evening? And of course the answer is that it is. But my rational self has plenty of experience now. This very familiar morass of self-doubt is now countered by (most of the time) a determination to ignore the voice of inner doubt, get a frock on and get out and about. And invariably, by the time I am strolling down the street, my gremlin has vanished and I feel at peace with the world; the only genuine battle remaining for me is to acknowledge, at the end of the day, that it really is not possible any longer to avoid removing my make-up and turning drab again. That, after so many years, there is any need for argument and determination to do what is so manifestly good for me as a person is perhaps the clearest testament to the self-harm accumulated during all those years of repression.

Arriving in Chicago at 3 pm on a Friday, I planned to head out for dinner. By the time my taxi had fought its way from O’Hare to my downtown hotel, it was nearly 5 pm. Somewhat weary after long journey, I nevertheless managed to shower, change and get out for dinner. As I hauled myself out of the shower and opened my make-up bag, the weariness was dissipating; by the time I stepped out into the warm evening air to walk a few blocks to Dearborn Street, where I dined outdoors, I was smiling, savouring the moment and looking forward to dinner outdoors.

I cannot rationalise how, given comparative freedom after so many years of repression, I experience this instinctive desire to do what is self-harming, in denial of the identity that I have striven to hard to come to terms with and to accept. I know from the many conversations I have had with friends that these sorts of feelings are not unique to me. I suppose that there is a kernel of rationality at their heart: I am a genetic man, and my physiology betrays that to even fairly casual observers. There is no sense in which I really believe that I can “pass” as a woman. But to undergo this transformation is not a piece of frippery for me, but something profound – for all that it also brings a lightness of spirit and a careless capacity to live in the moment and enjoy what the day brings. Whatever affront it brings to rationality, it also brings peace, contentment and wholeness. Sometimes it is necessary to set aside the fruitless pursuit of logic, for this thing, this self-realisation, transcends rationality.

2 responses to “Chicago”

  1. Karen,

    What a marvelous time you described. (I too love being femme in Chicago). Both photos are lovely, I like the white outfit the best. More importantly as a man who traveled with Tiffany I was drawn to your thoughts and reflections. The mind is always working thru the angles and aspects of our choices. At the end of the day I found allowing for my indulgences is how I find balance. Thanks for sharing with us.



    1. Thanks for your comment, Tiffany. Balance is the thing, as you say, although its not always easy to find it!


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