From CEO to Intern: How a 'What If' Year Changed My Life

Outwardly everything about Alisha Fernandez Miranda’s life seemed perfect - she had the career, the family and the home she’d always dreamed of. But inwardly she was in turmoil, unable to quieten the ‘what if’ questions about the paths and opportunities she had chosen not to pursue. Her solution to the dilemma was both radical and life-changing in pretty much every way. 

Assassins rehearsal

I rushed back to the rehearsal room, my arms laden with hot drinks threatening to spill over at any moment. Break was almost finished but I managed to sneak back in before the cast had to begin singing again. I handed the beverages out – a tea for Carmen, oat latte for Alex, an extra sugar packet for Bianca who took her coffee sweet – and sat back down quickly, poised and ready to learn everything I could about how to put on a Broadway musical. After all, besides getting coffee, learning about an industry was an intern’s primary objective.

On my way home that night, I called my dad to regale him with my victory – I didn’t get a single order wrong. A refugee who emigrated to the US from Cuba in the 60s, my father was no stranger to hard work – night shifts at the airport in high school, then trained as an accountant and had been crunching numbers ever since.

“So let me just get this straight,” he said. “You leave your husband and kids at home, and abandon your job as CEO to become an intern and spend your days getting coffee for actors?”

Yep, I told him. And I was loving every minute

Back in 2019, I was at a crossroads. On paper, everything was perfect. I was married to a loving and supporting husband, mother to eight-year-old twins and had a French Bulldog with a face just made for Instagram. We lived in a terraced house in Central London and I walked to work as CEO of a company I had co-founded, a philanthropy consultancy that helped people and companies give their money away. Approaching 40, I had the life I had always dreamed of.

Behind the scenes though, it was a different story. I was a hot mess. Sad and dissatisfied, guilty for feeling unhappy when I had been given so much. Desperate for a change but terrified of what it would mean for me, for my family, my career. I spent my entire life conditioned to succeed, to be the best. I had achieved it. But all night I would be awake dreaming about the other paths I might have explored, or the lives I might have led: my what ifs.

My idea to resolve this pre-mid-life crisis was unorthodox but as soon as it came to me, I could think of practically nothing else. I would chase these unchosen paths as an intern. A plan came together – take a series of mini-sabbaticals from my job and try my hand with work experience posts in the careers I had dreamt of working in: musical theatre, art, journalism, marine biology and more. The idea was to take a break from reality and come back, refreshed, revitalised and ready to continue in the life I had been working towards for years. I saved money, recruited friends and family into childcare standby roles, and started preparing everyone in my life for me to take a short break. It was a foolproof plan.

Applying for a job for the first time in ten years

I hadn’t applied for a job in almost a decade, and things in the working world had changed a lot in that time. Resumes had pictures and animation now? I worked on mine, crafted a heartfelt cover letter and sent it out to everyone I had ever met. I had so many informational coffees my blood basically was coffee and repeated more times than I could count: yes, I really do mean an internship. No, I don’t expect to be paid. Yes, I will file your papers and get you coffee. All I want is a chance to try something new.

This process went on for months with more rejections and disappointments that I could have imagined given my experience, but finally I got a break through a friend’s father: a dream internship, shadowing two musicals in New York. So I kissed my kids and husband goodbye and boarded a plane, ready to find answers, or myself or at least see a lot of great shows, eat a lot of street-cart pretzels and enjoy some well-deserved solo time. I couldn’t wait to spend March 2020 in New York City.

My internship journey had begun

Well. If you remember back to that fateful month, nothing went according to plan. I managed two and a half glorious weeks of coffee retrieval before all theatres shut down and I rushed home and into a lockdown that made my previous level of domestic responsibility seem like child’s play (remember home schooling? I was the worst at it).

Alisha on Retroglow Zoom Call

But in spite of the world turning on its head, I still somehow managed not to give up on my internship quest. I spent the spring of 2020 as a virtual intern for Retroglow, a dance and fitness company, fitting in market testing Kylie vs. Whitney Aerobics classes and something called Vogueing Yoga in between Year 3maths lessons, baking sourdough, keeping my existing company afloat and trying to not have a panic attack. When the UK tentatively re-opened I doubled down on in-person opportunities: I spent a month working with a contemporary art dealer, researching provenance and pricing priceless works, and another month at the stunning hotel and restaurant Kinloch Lodge on the Isle of Skye, where I ruined many a person’s holiday with my inability to remember the right room number or successfully carry a plate of food from kitchen to table.


The dining room at Kinloch Lodge

When I finished my fourth internship, I knew that my original plan – to slip out of, and then right back into, my normal life – wasn’t going to be possible. I had learned so much from my internships – not just the definition of impasto, which mushrooms are edible (never much on a hunch!) or how many one-handed press ups I could do (none); but about my strengths and weaknesses, my blind spots and the things I had sacrificed in my quest for constant achievement and success. By leaning into what I could be the best at, I ignored things that I was passionate about but unskilled at; I put aside creativity, learning in passion in favour of winning, praise and accolades. It had been great for a while. But entering my 40s, I knew it was no longer enough.


Alisha on duty at Kinloch Lodge

Now it’s all over

My internship journey has taken me places I never could have dreamed of going. By allowing myself to get comfortable with discomfort, to try new things that scared me, to fail without fear, I have reshaped my entire professional life. And my personal life too: I’m more confident and happier, constantly challenged and not at all sure of what’s coming next. Not bad for a Type-A overachiever who had a spreadsheet for everything.

Well, I still have a spreadsheet for everything. Some things will never change.


Alisha has written a memoir charting her experiences as an intern, My What If Year 

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