Re-Imagineer #2: Claudio Calo

You had a very high-profile career in advertising, marketing, communications in the Italian luxury market. We met when you were at Giorgio Armani. In your 40s, pre-pandemic, you decided to ROAR into a new direction. Tell us what prompted this major life change.

In my last corporate role I was the Global CMO of the Armani Group, where I stayed for just under 4 years. In many ways, I had accomplished what I had once set up as a career goal for myself… So maybe I hadn’t been dreaming big enough? Or was it just that in setting goals for myself I had not really considered my FULL range of passions and skills?

At 42, I realized I would get pretty bored pretty fast if I had just kept the same role or just moved to a different brand in the same role; and even a CEO role did not look like success in life to me. Would I just repeat the same motions for 25-30 more years?

I admitted to myself that to get there I had muffled the call of so many other interests, or at least I hadn’t paid too much attention to skills or areas that would have provided me with so much more personal gain and a sense of satisfaction. I left corporate and for a while, I decided I would not accept any other offer but only put myself in the position of being myself alone, with no roles, no titles, no immediate next step on the corporate ladder, no traditional job security to rely on (nor to use as an alibi).

All of a sudden I had the physical and mental space to look back at what I had left behind, as well as to every side: I had always said I wanted to be a writer but never wrote anything of note outside of my job parameters. So I took creative writing classes (I have a bachelor’s degree in literature) and started writing short stories, took drama classes which led to dancing classes, I started writing for some magazines, interviewing people from different walks of life… within two years I had written my novel, and got a deal to write a critical essay on fashion shows (my first published work, for Einaudi, Italy). I regularly train with a non-professional dance company, I teach a Fashion Communications Masterclass and I have taken several consulting jobs in fashion, communications, publishing and event management.

I feel the possibilities have only expanded and I am much more fulfilled than I was in my corporate role; I now set myself several goals as I see them fit, I don’t have a pre-ordained path to walk down. Publishing my first novel is next!

Since then, you have written a non-fiction book, and a novel and taught in a Master’s program in Florence, Italy. How has all of that felt as you jumped into what was a real action plan?

The best thing about it all is that there was no immediate action plan! I needed to make space to hear myself think and allow myself to desire new things. One day I woke up and felt I wanted to be a better dancer, so I started studying dance; the next day I knew I had to work on my writing and so I started writing short works of fiction which then developed into a novel—meanwhile I was reading more and more like I hadn’t done in years, and so on.

I am not saying these are not things that one absolutely cannot do while working an office job… But it’s really hard to start and push yourself if you don’t make space first, if you don’t question why you have devoted so much time to your corporate path and so little to everything else. For example, I have always been an avid reader but I believe we have all experienced that invincible tiredness that takes over when one opens a book at night after a 10-12 hour work day, while work emails keep coming in. And so we think, “oh I’ll just read a few books when I’m on holiday next…”

That’s not the quality of life I want. After so many years working in “luxury” I feel like the real luxury is to own your time and be in charge of how you manage your priorities, even allowing more space and time for what some might think of as “pastimes,” like reading and going back to study, over “work.” It’s not the same to do all of that “in-between” or “once I’m retired.” 

With such a big change in your life, did it give you an awareness of a new set of skills that will allow you to reimagine as an ongoing process between now and 90 or older? What is your best advice for people to step into their favorite future?

I think I’m much more aware of my possibilities and set of skills now. I will likely not become a professional dancer or write the next Harry Potter, but now I know that I can rely on other capabilities to sustain myself and make different career decisions if need be. I feel like I’m in the driver’s seat again—as small and improvised as my vehicle might be—as opposed to being comfortably sitting on a plush chair on the fast train to corporate oblivion, which I’m not driving.

My advice is to listen to yourself at all times, carefully and genuinely. Your desires and perspectives might change, they likely will in fact, and your happiness will come from very different answers you give to yourself at different times in your life.

When I communicated my decision to leave a big, well-paid corporate job without an immediate, obvious alternative, nine out of 10 people actually reacted with something along the lines of “I’m so jealous,” “I wish I was as brave” or “I hate my job but I’m too scared to leave.” To me it wasn’t bravery at the time, it felt inevitable. Question yourself often and answer honestly and kindly.