Life is Just a Game. Play it Your Way

Hello! Hello! Welcome to both my old and new readers!

Although none of you have been here before as this is a brand new re-design! I’m chuffed to bits with the look and feel and the UX. Lots of thanks to Livia and Tom of Three29Design for working patiently with me on customisation.

For those that don’t know much about me, I’ll quickly elevator pitch you in third person…

Luca Massaro is an entrepreneur, sports fanatic and boxing trainer.

A half Italian, half English South East Londoner, raised by a single parent with his two brothers on a council estate in Sydenham; Luca didn’t have much as a kid. However, the constant challenges he overcame growing up have empowered him into an incredible state of self belief and passion for helping others.

Luca is the founder of sports social media agency We Play, co-founder of startup social media league ExaLeague, a digital business consultant and a regular speaker on all things social media, entrepreneurship and personal development.

His mission in life is to inspire others to follow their dreams, believing anything is possible in today’s digital world.

Back Then

June 13th 2012. That was when I wrote Sacrificing Security to Build the Legacy. At that point I was approaching my biggest challenge yet and that would be the last time I would write for this site.

I launched We Play at that point and knowing my impatient attitude and lack of commitment to any single project, it was my new mission to focus on one business and one business only. For those that know me, know that I have lived quite an erratic professional lifestyle jumping from idea to idea, spread out thin across multiple projects and never really getting the best out of my ability.

So We Play began by picking up where all my freelance work left off. I was focusing on helping entertainment brands connect with fans using social media; via analysis, strategy development, installing various engagement tactics and helping them execute. Whether it was an agency or a client, it didn’t matter. The money was good and the commitments were small. The challenge I would face was how to differentiate from the gazillion other social consultancies offering everything to everyone and promising the world.


Uncertainty is potentially the worst thing in life. Not knowing who you are or what your purpose is…

Fast forward to December 2012 and I happen to find myself travelling around Vietnam and Thailand. I left my business in the hands of a few of my trusty team and spent two months on sleeper buses, in shared accommodation, riding scooters up mountains, visiting rice factories, chilling with locals, eating bugs, having massages (no happy endings), training Muay Thai boxing, learning how to cook Thai food and spending New Years on a beach.

Me-VietnamFunny thing is, it would take another three months of being back in London for me to actually realise how much of an impact that trip would have on my life.

When I left University in 2009, I had a serious desire to achieve, but no direction. There’s no plan of action, no goal setting and no guidance when you get into the ‘real world’, so we just do.

From Intern at Ctrl.AltShift in 2009 to Social Strategist at Think Jam to Community Manager at Gumtree to Digital Manager at Chelsea FC and to Head of Social Media at Target Media by 2011; I climbed the ladder very quickly. My salaries and day rates were almost doubling with every change of employment. At some points I had more money than I could spend and more pairs of trainers than I could ever wear, (I love trainers) but I felt a tad empty.

The last year has been the most eye opening of all my years. Uncertainty is potentially the worst thing in life. Not knowing who you are, what your purpose is, what your strengths are or in which direction you should head. It has plagued me since I was 22 when I set up my first venture, which was a society at Portsmouth University that helped talented students connect with other talented students. It was actually back then that I knew I had a purpose to connect and help others, but I ignored it.

I wanted to change the world while my friends couldn’t afford to change their boxers

Growing Up

I get told often that I am mature beyond my years, which is great… I guess. Usually at a networking event, where most people are there to source some form of inspiration or opportunity. What generally happens (without blowing my own trumpet), when people talk to me, is a small circle forms. It appears I have the ability to create an impact; so I am told. This was what someone told me recently actually when I asked them…

“What is it that you remembered about me the first time we met?” I asked. “You leave an impact.” They said.

There is a downside to this maturity and wisdom, being that I feel like I grew up too fast. I missed the parts of my twenties that involved not giving a shit, being passive and casual instead of serious. I’ve always been quite serious about my goals. Even at University, I was trying to inspire my fellow student pals to do more with their time, considering lectures were never more than 4 hours per day. It was a frustrating period.

I realised that I wanted to change the world while my friends couldn’t afford to change their boxers. I then grew apart from those that I was closest with. Years past by and although I had elevated my career to this position of power; I never felt content. I didn’t feel like I deserved what I was getting, I was just doing because I could and in some instances I felt like a fraud.

With an analytical mind, I am always thinking. Rarely switching off. I’m constantly wired with the cogs in my brain churning information into potential new innovations. However, the stress that accumulated over the years resulted in tension and anxiety that eventually led me to two MRI scans on my brain because of the symptoms I was having. I’ve just had the second scan and although they found come form of cyst, it doesn’t look threatening. The downside is that any hope of a future boxing career appears out and light sparring is as rough as I can take it. The plus side is that I was told I have ‘the biggest creative brain the neuroscientist had ever seen.’ Score!

I have always believed that challenges are placed in front of us to be challenged.

Being Uncomfortable and Guarding Your Milk

I never want to live with regrets, not now and definitely not when I am older. So it’s in my interest to take risks while my body and mind can handle it. So he says…

Challenges are placed in front of us to be challenged. We all need to be taking risks, every day, mixing it up, challenging ourselves, venturing into unknown territories. Mel Robbins spoke profoundly in a famous TED talk about this very subject. We crave exploration. Everything about us as humans, grows. Fact. Our hair, nails, cells and our heart and soul also needs to grow. Therefore being stale, stuck doing things we don’t want to do or living in unhappy environments; is bad for the soul.

Doing the same things every day is like torture to me. Don’t get me wrong, I go boxing every Monday, Tuesday and Thursday, but the sessions are always different. If we were doing the same routines, pad drills and exercises every time, i’d have thrown in the towel (pun).

That’s why in fitness training, we’re told to continuously ‘shock our bodies’. Performance development is based upon doing things you’ve never done before, conquering new feats and pushing boundaries. It’s with comfort that comes complacency and with complacency comes staleness and with staleness comes laziness which will ultimately lead to lack of anything productive being achieved and resulting potential failure.

You have to be prepared that at any point your milk could be stolen (your milk is your comfort – partner, job, heart, finances, possessions, dreams). People are selfish. That’s right. All people are selfish, but some are more so than others and have little consideration for the anyone but themselves. These people are out to steal your milk.

You know what I am talking about… you put energy, time and resources into something you believe in. It goes to your plan for a while but you get too comfortable; you take your foot off the gas. You get a knock back and maybe the people who you trusted and relied on aren’t who you thought they were. That’s damaging to the system. Some never recover from this kind of impact. Others learn from it.

This isn’t paranoid thinking people, it’s preparation. Metaphorically, prepared people see the punches coming before you’ve throw them. The eyes, the neck snap, the shoulder twitch, the hip rotation and even the foot work; in the ring, these are your tells. In real life, we have to look out for these signs. Comfortable people get sloppy, lazy and ignore the tells.

You have to be prepared that at any point someone could steel your milk

Test of Character

I’ve had plenty of knock backs. I guess, that because I have ventured into the unknown, on my own and tested myself on so many levels over the past 7 years, I would say I have had more knock backs than the average 28 year old. Mentally, emotionally and physically; god knows I have asked for his help on many occasions. Each knock-back has chipped away at my being, creating a cavity that sent me into a daze of sleepless nights and anxiety. But time is the biggest healer and as it passed, I input those learnings into my next adventures ensuring that I don’t make the same mistakes again.

What I learned is that it’s when we’re down on our knees praying for a saviour, that we are tested; mentally, emotionally and physically. Which of us will push on and which will cower into the corner? Do you hit the deck when you smash against the wall or do you smash the wall down with your sledgehammer? (Metaphor – I don’t actually expect you to walk around with a sledgehammer).

I’ll tell you, having my MRI scan and getting the results was one of the scariest things I’ve ever had. The Doctor calling and saying, “we need you to come in” but leaving it there, he didn’t want to explain on the phone. Then when I went and met him later that day, saying, “we’ve found something.” My heart sank. “There’s a cyst the size of a boiled egg.” I’m like, WTF! “I’d advise you not to continue with your boxing,” I was told. Basically, if I get punched in the head they don’t know what will happen. Cue the blank stare.

It’s times like these when we are really tested. How do you react to potentially life changing news? That’s where we realise what we’re actually made of. This isn’t a movie people. This is your life! All of these challenges I have to face are part of my journey, so it’s in understanding this that I begin to paint my next picture.

Energy, Greatness and Unleashing Your Passion

I believe in human energy and that greatness is achieved when energy from multiple sources of inspiration collide. I crave for deep connections with people that will enable us to achieve together. Like magnets, I believe energy is attracted to energy. 

So here I am. With a renewed focus and a certainty that I know my purpose is to help others reach their goals, so that together we can all achieve. That for me, is what it’s all about. My contribution has begun, I know my strengths, my weaknesses and that I have the ability to ‘make an impact’.

I have re-created this site with that in mind. To showcase my skills, to present my ability to understand people and businesses and the way in which digital technology influences our decisions. To display my work and case studies for those that I have delivered for. To list the events that I will both speak at and attend. To help people and brands, reach their goals; because my journey began with a simple vision to share, and with the means of digital, I was able to express myself, share my voice and connect with others. I will also give a section of my site to those of you out there that have inspired me also (see Industry Spotlights).

So now I push on, with a much clearer mindset and hopefully it’s on a journey that others will join me on. To read not just about my story, but to share with me yours. To get inspired and to reach out to others on collaborative efforts. To reach out to me with your ideas. To ensure that we are not just existing; we are living.

My questions to you are these:

  • What are your passions?
  • Are you on your way to achieving your dreams?
  • Do you have an energy, an innate desire to do something but you don’t know what?
  • Has someone stolen your milk before?
  • Are you currently down and wondering how you’re going to get back to your best?
  • Do you want to collaborate with other inspiring people so that you can reach higher levels of success?
  • Just want to talk with someone?

If any of these questions resonate, send me a message and i’ll get back to you.

If this content inspired you, fill out your details and join me on my journey