My wife and I are in our late 60s. The past 20 years have felt like treading water, as all my funds are tied up in a property that, for complex reasons, I am unable to sell. We are both creative. Over the past year or so I’ve made some improvements to our house, things that make people say wow. I enjoy seeing their pleasure, but their praise isn’t hugely important to me. In fact, I am somewhat reclusive. I do not enjoy being part of a wider community and I’m content with a handful of close friends.

Last year my father died, and after a period of despair, during which I found myself contemplating suicide (I did not share this with my wife), I turned first to Samaritans, then a therapist.

Another problem had been my love of cross-dressing, which never sat easily with my wife, though she was accommodating to a degree. I was able to visit the therapist “dressed”, and with his help I raised the subject again with my wife. To my surprise and relief, she agreed I could dress more in her company, though she asked that it only be in the privacy of our home. This lifted a great weight from my shoulders.

My dream is to sell up and launch myself into another building project. I’d also like to travel. All this is possible, if only I could sell this house. I feel as if I’ve wasted so much time and wonder if I have mild depression?

I went to the British Psychoanalytic Council-registered psychotherapist Elena Mundici. We both felt the death of your father has been a catalyst, as it often is. “Death of a same-sex parent can bring up all sorts of feelings about transience and mortality,” explained Mundici. And those feelings can absolutely be “what have I done with my life and what am I going to do with it?” We also discussed whether your mourning has got stuck – this can lead to depression. “I wonder if by going to the ‘next project’ you’re trying to avoid the pain of these losses,” said Mundici.

Mundici felt your house sounded a bit like a “golden prison – your friends are wowed, but you feel trapped”. She said there were lots of external explanations for perhaps something that was going on internally for you: “There seems to be a discrepancy between the beauty outside and the bleakness you describe inside.” Who is the real you? I found lots of contradictions in your letter.

I asked how relevant the cross-dressing was. “It made me think of an alternative life, the desire for something that feels inaccessible, perhaps,” said Mundici. “There seems to be an energy in you, but it’s behind a screen. But it’s important you were able to share this with your wife. Secrets can be painful.”

We don’t know if you have mild depression, but your suicidal thoughts are to be taken seriously – I’m pleased you’re seeing a therapist.

I asked Mundici: what next? “As George Eliot said: ‘It’s never too late to be what you might have been.’ There seems to be a lot of beauty, creativity and resourcefulness in your letter. You went to therapy, you told your wife, you’ve written in. You’ve chosen life and there’s lots of capacity to create, but maybe now is the time to turn your attention to your internal landscape rather than the next building project. You could be your next project.”

You say your house won’t sell, but I wonder if selling it might force you to think “what next?” in a way that feels quite scary rather than liberating? I think taking Mundici’s advice of attending to your internal landscape is really important: what makes you feel most like you, and will selling your house help you achieve it?

In the UK and Ireland, Samaritans can be contacted on freephone 116 123, or email jo@samaritans.org or jo@samaritans.ie. In the US, you can call or text the 988 Suicide & Crisis Lifeline at 988 or chat at 988lifeline.org. In Australia, the crisis support service Lifeline is 13 11 14. Other international helplines can be found at befrienders.org.

Every week, Annalisa Barbieri addresses a personal problem sent in by a reader. If you would like advice from Annalisa, please send your problem to ask.annalisa@theguardian.com. Annalisa regrets she cannot enter into personal correspondence. Submissions are subject to our terms and conditions. The latest series of Annalisa’s podcast is available here.