Ask HN: Should I go on sabbatical even if I'm afraid of it?
Hello guys, I'm a 39-year old Italian software engineer with 10 years of experience, and I'm afraid of going on a sabbatical.

My background is quite different from my peers: even though I have a respectable and loveable family, when I was a young adult, I left my studies after secondary school and made a lot of mistakes and wrong decisions that eventually led me to commit different crimes, including a robbery, for which I spent some time in jail.

After that experience, I was in my 20s, finding a job was hard, and I only worked as blue-collar for small-term jobs.
I also started suffering anxiety and panic attacks, and I was afraid of many things, especially working and finding a job.
While working temporarily in a call center, I decided to go to an evening school to have more options on the table, and when I was 25, I successfully took a high school diploma in IT.

My goal was to work as a computer technician since every other IT-related job was unavailable to me; I had a criminal record and a barely fresh diploma, while my peers were probably coming out of university with a Master's in CS or related. It was too late to dream of something better. My family continuously told me: just be humble and satisfied with what I achieved.

I was not.

I chose to continue studying, and during the next few years, I completed various evening professional courses in Sys Admin, Networking Configuration, and a Cisco CCNA.
When I got the first offers in the field, I was terrified to accept them, and I realized that configuring computers and networks was boring.

So I started to study PHP, HTML, and CSS (other evening courses), tinkering with my first websites.

A teacher noted my passion and offered me a job at his company: at 29 years old, scared as hell, I took my first job as a programmer for an Italian broadcaster, Radio 105.
Throughout all these years, anxiety and fear never left me.
I even had terrible impostor syndrome, constantly feeling like I was in the wrong place, doing bad things.

Time went on, I changed jobs, and suddenly I had the opportunity to work for eBay: me, a guy with this past, working with real software engineers!
That's when I realized that maybe I was not so bad, and while working there, I searched for help to heal my uneasiness.
I started to do cognitive therapy and, recommended by my therapist, mindfulness. Along with some SSRIs, this helped me to be more self-confident, calm and less restless.
This new state of being enabled me to prepare for my next journey: five years ago, I decided to try for a Bachelor's degree in CS while working as a software engineer for a startup.

It was extremely challenging, but I was happy, and in the end, I was successful: last April, at the age of 39, I graduated with a good vote, and my dream came true!
While studying, I realized that, from those distant years when I decided to take my first step into trying to change my life, I never stopped learning and working and that I was, in some ways, tired of giving my 100% to be successful.
So I started dreaming about a sabbatical after graduation to take some breath, rest, travel (another thing that, in some way, scares me a lot) and enjoy life. Even in Italy, where the work ethic is quite old and conservative, and things like sabbaticals are frowned upon, it couldn't be that difficult to find another job as a programmer! That's what I thought.

And now that I'm there, I'm terrified.
Anxiety, fear, and uncertainty like in the past: what if I could not get another good job? What if I'm too old to be a programmer? What if I cannot return to work and feel fatigued after a long period of rest?
My therapist told me that maybe it's just my self-conservative side: I only discovered that this sabbatical is the wrong thing to do.
I'm not totally sold on this theory, so I'm here, asking for some advice and help.
Sorry if this post is too long, but I had this thing to say, and I hope this is the right place!