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My dream job no longer feels so dreamy…

Even if we were lucky enough to land our dream job, it doesn’t guarantee that it will feel like a dream forever. Companies and people grow and evolve, sometimes in different directions.

Unleashing your best

Maybe you don’t feel engaged anymore or fulfilled by the work you are doing.  However, you also don’t want to quit your job.  Maybe you like the people you work with or the culture.

You feel stuck, maybe even trapped, because it’s not all bad, but it’s also not all good. 

I’ve been there and I can share with you that there’s good news!

You are just one side hustle or passion project away from tapping into a great source of fulfillment and unleashing your engagement in all things you do!

My name is Roger Osorio and I am a Reinvention Coach. I help corporate employees who feel disengaged or unfulfilled with their day job to launch a side hustle or passion project that aligns with their values, passion, and purpose so that they don’t have to quit their jobs.

I have been where you are…

Early in my career, I discovered that I had my own definition of success and it looked nothing like the traditional version I inherited. Inspired to pursue success on my terms, I made the scary decision to quit my corporate job and launch my first reinvention. Navigating my way through the Great Recession, I learned how to make the impossible possible by going from national account sales manager to a high school math teacher without any teaching credentials or relevant degrees.

On my journey, I also learned how to turn terrible setbacks, like getting fired and laid off, into life-changing opportunities like becoming an international speaker, an executive coach, an Ivy League instructor, and an entrepreneur.


About Roger

Roger is an empowering and energizing coach who has worked with over 3,000 professionals, students, educators, executives, athletes, and entrepreneurs to define life on their terms and take massive action!

Roger’s coaching journey started with one of the most unlikely clients – math students. 

After he began to apply coaching to his tutoring clients, his clients’ parents called to ask why their kids were suddenly interested in their math homework and asking for more tutoring hours.  In that moment, he discovered that coaching could empower people, even those who struggle the most, to get excited about overcoming challenges!

Since those early years of coaching practice, Roger has gone on to coach thousands of entrepreneurs around the world through his work for organizations like Techstars.  He has also served as an executive coach at IBM, coaching executives, managers, and professionals around the world.  At IBM, Roger taught a coaching certification course for IBM leaders who wanted to apply coaching to their managerial style.

At University of Pennsylvania Roger has coached graduate students, since 2018, on how to design and drive educational startup ventures from concept to creation.

Today, Roger coaches unfulfilled or disengaged corporate employees to build side hustles or passion projects that move them closer to a life aligned with their values, passion, and purpose.

Roger is a master at creating safe learning spaces and environments where people can unleash a growth mindset and break through their limiting beliefs.  His style and approach has inspired thousands of people to believe in themselves and make the impossible possible!

How can I help

There are many reasons why you might consider reinvention coaching, however, here are some specific examples in case you aren’t sure if coaching is right for you.

To help you build a life aligned with your values, passions, and purpose, I offer coaching packages  of different lengths so that we can work together to launch your passion project or side hustle!


All of my coaching packages include: 
Complimentary Access to the School of Reinvention Community for 12 months (valued at $1,164) - this is an online platform for all of my clients where you can learn reinvention skills, ask reinvention questions, work on our projects together, and stay engaged in between sessions.
Signed copy of my book The Journey to Reinvention: How to Build a Life Aligned with Your Values, Passion, and Purpose (a $47 value)

Of course, I totally understand that you might want to test things out first and I have a one-time introductory offer for 3 sessions for $997  that we can discuss on a discovery call. 

Imagine Cristiano Ronaldo or Michael Jordan without a coach… You can’t, right?

Roger can be your catalyst to unleash your hidden greatness!

The graveyard is the richest place on earth, because it is here that you will find all the hopes and dreams that were never fulfilled, the books that were never written, the songs that were never sung, the inventions that were never shared, the cures that were never discovered, all because someone was too afraid to take that first step, keep with the problem, or determined to carry out their dream.
– Les Brown

Don’t let your passion project or side hustle dreams go to the graveyard.  Live life on your terms and just watch how your ideas go from dreams to reality!

Let’s talk for 30 minutes about your ideas!

Still not sure if reinvention coaching is right for you?

Let’s get on a call to talk about your values, passion, and purpose and determine if I am the right guide for you. Even if I’m not the right fit for you, I’d love to help you understand what coaching can do for you.  Use the button below to book a complimentary 30-minute session with me.