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After working at jobs he liked, Dillan DiGiovanni took the chance and jumped into what would become his First Love.
Five years ago, the life I live now was nothing more than a dream. When I became a coach and speaker, I had no safety net, no guarantees and nothing but sheer will and determination. In fact, when I started doing it, I never actually planned for it to become my full-time career, let alone something I truly loved and made a living doing. I just knew I wanted to try and didn’t want to spend another day wondering if I could actually do it.
For the first time in my life, I Â LOVE what I’m doing each and every day. It took an idea, a bunch of courage and a healthy dose of risk-taking, but I’ve developed a love affair with my career and I want everyone to feel this way.
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The truth is, I first became a coach to have side cash in addition the salary I was making at my 9-5, non-profit job. I didn’t really have the courage back then to “go for it” 100%. I knew I liked helping people and I had a certain about of knowledge from working in  health food stores for many years. I loved the job I had but there were aspects that were missing, things I loved and cared about that I wasn’t doing. I sat each day weighing the reality of how good I had it with the possibility of what would happen if I took the leap.
Five and a half years later, I’m living the life of my dreams. I never thought it would end up this way, just like the end of the Justin Timberlake song, “Like I Love You”. But like he says, my life is the way it is because I am doing what I was “destined to do”. I say this like it’s easy. It isn’t easy, but it IS worth it.
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I wasn’t raised to think of life and work this way. I was raised to be what my college professor called, “gainfully employed” upon graduation. I choose to major in education because it seemed like I would always have a job. I did get a job as a teacher and then left for a few reasons, in part because I went on furlough for 3 months out of each year and had to stretch an already-meager salary even further. When some people say, “Hey, you get summers off!” I don’t think they realize teachers don’t actually get paid during that time.
So, I quit, three months shy of tenure. It was one of the first times in my life I “leapt” and really defied a pretty conventional social norm by walking away from a guaranteed meal ticket.
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I thought I had an issue with focus and follow-through. I thought I couldn’t make up my mind. It wasn’t either of these things. I was an entrepreneur through and through, I just didn’t know it yet.
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From teaching, I went on to work in health food stores full-time and learned a ton and developed a tremendous competency with supplements, natural products and complementary healing modalities. Then, I became a advisor for youth and from there, I moved to a job as a program director for youth and young adult programming. It was a great job. I learned a lot and gained a ton of experience. And then, the familiar feeling crept back in. It seemed I had a certain pattern where I would get into a job and love it and then feel the need to move on.
I thought I had an issue with focus and follow-through. I thought I couldn’t make up my mind. It wasn’t either of these things. I was an entrepreneur through and through, I just didn’t know it yet.
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Until I started, I didn’t know it was possible to actually spend my days doing what I love, and getting paid for it. I didn’t think it was realistic. I didn’t think it was responsible. I thought it was more appropriate and socially acceptable to stay somewhere safe that had great benefits, great people–a place where I did great work.
The doubt that lingered was unyielding. I kept wondering and daydreaming about working for myself, traveling around, making my own schedule, working from coffee shops all day and being my own boss.
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I want to get to the end of my life and say I gave it everything I had.
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I did end up leaving that job and jumping into coaching mostly full-time after becoming certified. I took the leap, the leap that many fear and most never take. It became a leap that was not only rewarding but financially lucrative–which of course helped me feel more confident. When I became a coach, I was facing over $13,000 in debt, I had no savings and lived paycheck to paycheck–on a pretty decent paycheck at that. I was living well above my means with no respect for my time, money or my lifestyle habits. In my second year in business, I obliterated my debt, and made a significant profit.
Five years later, I have a larger savings account than I ever had with any previous ‘regular’Â paycheck.
And that’s just talking practical stuff. It’s the stuff people worry about, for good reason. It’s the practical concerns my clients have when they face a similar decision.
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But I haven’t even told you about the people I work with and the things we accomplish in their lives. I haven’t mentioned the moments I sit on the phone or in a coffee shop booth and listen to people share their deepest truths, and honest fears. And then I watch the transformations they make in their lives, transformations I know well from walking my own talk. Working for myself and pursuing my passion forced me to grow along the way. Anything that wasn’t connected to my dream or helped me move it forward had to go. This was huge growth for me, Â to learn to let go of perceived ‘guarantees’ in life. That’s why I think my clients feel so supported by me, because I tell them these stories. Each obstacle they overcome, I sometimes surmounted myself mere days or weeks before.
I read emails and messages from people who learn to love themselves and their lives more, with ease and grace. I give talks and workshops and bring crowds to laugh and cry in the span of an hour as we explore food, life and love.
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When I was 14 years old, someone came to speak to my high school and I set it as an intention to become a speaker. I wanted to motivate and inspire people, but then I lost sight of that dream career for something more practical, to follow the rules.
“There are people who put their dreams in a little box and say, ‘Yes, I’ve got dreams, of course I’ve got dreams.’ Then they put the box away and bring it out once in awhile to look in it, and yep, they’re still there. These are great dreams, but they never even get out of the box. It takes an uncommon amount of guts to put your dreams on the line, to hold them up and say, ‘How good or how bad am I?’ That’s where courage comes in.” -Erma Bombeck
Fortunately, years later, health coaching reminded me of this dream I had to be a speaker and inspirational presence and I pursued it with fervor. I decided it wasn’t going to be a dream deferred but something I would accomplish–or at least try as hard as I could to accomplish. I wanted to live a life I loved, not just fill my days with being busy and following rules so I could fit in and have a retirement account. I know too many people playing that game who are broke, sick and miserable anyway. People like that contact me to become my clients, or they choose to keep being broke, sick and miserable.
I made the choice, and continue each day, to pursue my dream. I want to get to the end of my life and say I gave it everything I had. Every time I come up against the temptation to bow out, I remind myself of how far I’ve come, how hard I’ve worked to make it this far. I think about all the ideas I had and what I learned along the way as I Â manifested them into reality. Damn, all those amazing lessons I wouldn’t have learned otherwise.
I even taught myself some basic HTML coding to build my own sales pages. Enough said.
Living a life you love isn’t impossible, it’s not just for the lucky few. It simply comes down to this: are you doing what you’re destined to do?
If not, what would you need to do to make it happen? Consider that you CAN love your life. If I did it, anyone can.
—Photo tricky (rick harrison)/Flickr
Find Dillan at www.dillandigi.com
On Twitter @DillanDigi


