19 Career Changes and a University Degree Later, I Became an Entrepreneur

This is my winding story of how I grew up with a love for music, a need for a plan, went through many career changes, got a degree, quit my job on the day I was being promoted, and finally went entrepreneur full time.

My name is Alexander J. Yolevski, and since I can remember, I’ve always had a plan. At the same time, those plans rarely unfolded like I thought they would.

I frequently find myself becoming entwined in different interests and opportunities, overwhelming myself with what I could be doing for the rest of my life.

The problem: I want to do everything. Perhaps I have too wide of an interest spectrum. Or do I get bored easily? I try to do too many things at the same time, leaving myself in overdrive, and eventually, in potential burnout.

We all try to create a road ahead of us to walk on. Never mind the obstacles; it’s the road that we need to worry about. The ever-changing path makes the road itself our biggest obstacle in life.

I’m sharing this with you for a few different reasons:

  • Learn from my story.
  • Know that you won’t always be sure of what you should be doing.
  • The path towards entrepreneurship isn’t always clear.
  • Want to hear other people’s stories and experiences

Let me explain my experiences, and where I am today. I’m warning you, there are more than a few twists and turns in it.


Even as a child, I have always had a passion for the arts.

Whether this be playing music, singing, dancing (no, I can’t really dance and look like a sane human being at the same time), acting, etc.

Since then, that’s probably the only thing that has remained static in my life.

I know that I love music and it will always be a part of me. I would love to do music for a living.

However, I also want to achieve a whole lot of other things in my life, which require a more substantial amount of income.

Yes, I know what you’re thinking. “You have to give it all up to do what you love. You need to sacrifice” You know what?

You are probably right.

I’ve thought about it, and always believed that if I just stopped and quit everything, I would eventually become successful in my music career. If you work hard enough at something, and love it enough, you are bound to achieve.

I mean, that’s how all these “rags to riches” stories occur, right? I’ve even gone to the extreme of saying, “If you’re not poor, or don’t become poor, you won’t become famous”. Of course, if you are extremely wealthy, that can help too.

I’ve also had these fraudulent beliefs that if you are middle class, you are probably going to stay middle class for the rest of your life.

You hear of “rags to riches”, but do you ever hear of “Ralph Lauren to riches”?

Well, fortunately (for middle class people like myself), they exist. They just don’t get publicized as much because, well, they make for boring biographies.

I would much rather read about someone who slept in a car (not their own), did blow, prostituted for the blow, crashed parties for free food, and never showered, until finally someone said “this kid is fucked, but he’s extremely talented, you need to check him out.”

Nonetheless, there is hope for the middle class.

Yes, I understand sacrifices need to be made (and they have been in the past), but while I love music, there are other interests which can not only act as a reasonable source of income, but can help maintain my music interest as well.

More importantly, according to most naïve people, they are interests “you can make a career out of!!” (sarcasm), although I couldn’t care less about that.

I want to be able to enjoy life, by doing what I love. Who doesn’t? But if you are doing what you love, while scrambling to find your next meal, then are you truly enjoying your life?

Sure, large success can occur from taking large risks, but large success also comes from working hard and being consistent. Nobody said success comes from quitting everything else in your life.

Anyways, let’s continue down my ever changing road.

We’ve established that I have, and always will, have a passion for creating music. However, as I began to explore secondary routes for my life I decided in elementary that I wanted to become a lawyer. This isn’t my bio (although it’s almost turning into one), so I’m not going to elaborate on everything.

In high school, I then realized I had more of an interest in psychology.

This interest was sparked from a grade 11 English class, talking about Carl Jung and Freud.

In grade 12, after taking my first philosophy course, I became mesmerized and intrigued by theoretical debates, and theories of our world (in existence or not). I liked that it made me think.

For whatever reason, while I was applying to university, I decided to take the psychology route instead of philosophy.

I saw more applicability with psychology; a larger window for career development.

I figured I would become a psychologist, or maybe an occupational therapist, perhaps a counselor. I switched between these interests within my first two years of university.

During University, I Was The Lead Singer Of a Band Called Times.

We ended up being featured on a reality show on MuchMusic. We did quite well for a band with so many things going on, other than our music (school, work, side projects etc).

We were able to sell out Much Music for the live airing of the show. We also released an album in iTunes and HMV. This continued for almost 2 years. However, soon after our CD release party, we slowly but surely parted ways.

During my last year of university, I had become more interested in Philosophy again, taking more philosophy courses, but only out of interest.

In addition, I have always been fascinated by teachers and what they do, and I wanted to become a professor; or high school teacher (funny coming from an entrepreneur right? I)

So Get My Masters, Then PhD, Publish A Book, And Become A Professor.

That was my plan. Unfortunately, I became intimidated. I was intimidated by the amount of educational years required to become a professor (and the amount of income-less years I would have to endure before anything would stabilize in my life).

In addition, I was intimidated by the very little demand for teachers in Ontario, and the contrastingly high numner of applicants trying to get into teacher’s college.

Just to back track a bit, at this point, I have been working at Apple for about a year or so. During my employment there, I played with the idea of becoming a mentor or trainer of some sort. As much as I admire and love Apple, however, things became a bit stale and robotic for me.

At one point, I figured Human Resources seemed like a great opportunity to apply my psychology and educational background.

When I was offered a position in a Human Resources Department, I viewed this as the foundation for a potential career.

Also, it was my first stabilized, consistent, Monday to Friday, 40 hours a week, standard job.

This is where things get a bit haywire.

I was successful in my HR role, and the opportunity had been more than I could ever ask for. I’m sure any graduate would kill for the chance to evolve and develop in the field of HR.

However, with weeknight and weekends free (and no school work to think about at home), I began pursing multiple interests and possible side careers.

This would include everything from my solo album, photography, video production, and even a tomato sauce business.

I had gone as far as establishing and certifying two separate businesses. One was for the tomato sauce business, which quickly lost its fire and the other sort of became of the beginning of what I do today.

The second business, initially, encompassed photography, video production, logo design, and web design all into its services being offered. I had gone as far as buying all the required hardware and software as well.

It is also registered with the government. Unfortunately, I realized my interest for the graphic design part of it began to fade. Video production became boring, when it wasn’t my own content, as well.

As my own company began to downsize in what it had to offer, I was happy to sort of “trim the fat” and just slim down what it was that I truly wanted to do. Music was still there, and the feedback on my pictures being sold as of that week, had been nothing but positive. However, I needed something more. It wasn’t enough.

I am a huge Toronto foodie, and was a food critic for blogTO, for a short period of time.

Unfortunately, the meals soon became more costly than my pay.

I also still wish to write and publish a book at one point! (I’m not going to elaborate much on this either).

I mentioned earlier that I always wanted to become a teacher, but remained intimidated by my chances of becoming one. Nonetheless, as great of an opportunity my HR position has become for me, I could no longer picture myself wanting to develop and learn more within that field. I love to learn.

When I realized that I no longer wanted to pursue anything new within HR, I knew it would no longer be a career option for me. Whether I would be successful or not, I would not be happy. So I quit my job the day I was offered a promotion.

I Decided To Enroll Into Teacher’s College and Become A High School Teacher.

I had one and a half months left in my employment in HR when making this decision, and was extremely excited to pursue a true passion of mine. Why was I no longer intimidated? Because if I work hard enough at it, and I truly love it, it will work out and I will achieve some sort of fulfillment in my life through this choice; this career change.

So go back to school, get certified, and become a teacher. Good plan right? I’m done. I’ve finally figured out what I want to do, and what I will be doing, for the rest of my working life — YAAAYY!!

Not so fast.

Did I Mention I Am a Bit Of A Real Estate Hobbyist?

Yes. I am fascinated and interested in the pre-construction market happening in Toronto. I love finding out about new downtown condominiums, architectural designs, floor plans, VIP list etc.

Did the thought of getting certified as a real estate agent cross my mind? I’m sure you know the answer by now. Yes!

But not then, considering I was trying to get certified as a teacher first. In addition, I didn’t know how much more change my family and friends can take at the moment. Maybe I can get my license in the future, and do some real estate during the summers? (You see where my mind goes sometimes and how it drives me crazy?).

Nonetheless, I’ve already invested in a condominium, however, with full time school coming up, and less income, this is going to become increasingly difficult. I reached out to a few contacts to find an opportunity for some part time work during school.

Finally, There Was One More Crazy Idea Left Up My Sleeve At That Moment.

Another thing I have always wanted to do, and I feel like it’s in my blood to do so because my family has owned a few restaurants before, is opening up my own restaurant. Of course, you need money to make money, and the costs of opening a restaurant are much more than I can handle at the moment.

As a result, I had this food truck idea that I had begun to pursue in terms of research and finding out what I need to get started. This never completely panned out because of a lack of financing, partnership etc. Nonetheless, it’s something always had in the back of my mind.

I went back to York University to complete my undergraduate thesis (after already graduating with a BA in Psychology a few years ago), to keep the opportunity to get into a post-graduate Masters program at some point in the future.

I spoke to various professionals in both the psychology and social work fields, as well as professor at various university institutions. What I loved about psychology was the counselling aspect of it.

However, in the “real world” it is the social workers who do the counselling and the psychologist conduct more of the diagnosing and assessments. This is what made me decide to pursue a career in social work, and why I was applying to a Masters of Social Work program.

In fact, I was determined to attain all straight A grades during my final thesis year so I have a greater chance of getting into the program I want. My plan was to get become a certified Social Worker and work in high schools (eventually universities) to help students with their occurring dilemmas related to education, engagement, and anything else.

In addition, I was volunteering at Rogers Raising the Grade with Boys & Girls Clubs of Canada, working with youth and their engagement in learning with an emphasis on digital literacy.

While I was successful in completing a full university year with straight A grades, my interest dwindled as I realized the limitation in responsibility for this field depending on your position.

In addition, people with PhDs were taking jobs away from those with Master degrees because they were unable to find any professorial jobs themselves.

I came across and was offered an amazing and unique opportunity to be a part of an exciting company growing ever so rapidly called EventMobi.

I really felt that could be a huge career shift and commitment for me, and a chance to truly contribute and put my footprint in something special.

It was a company I can be proud to be a part of, and be passionate about, rather than just being another employee number.

After an amazing and memorable seven months with EventMobi, another promotion and salary increase, I was approached by a previous client of my creative company that I pursued full time then part time for a while.

This person simply put, gave me an offer I could not refuse.

It was an opportunity that was customized to my professional wants and needs, my career goals, and my personality. It also allowed me to pursue something I have always wanted to do, and assumed that I would do one day, but not this soon; my own business.

It made sense professionally, personally, and financially. While I never had any intention of leaving EventMobi for a while, I knew I could not pass up on this opportunity.

You can read about how it all started from a single tweet right here.

That was almost 3 years ago and where I am now.

I am run a business callled Yolevski Creative Media. We help entrepreneurs start and grow their businesses online with creative content and persuasive writing. Services include online marketing strategy consulting, copywriting, web design, and graphic design.

I have never been more excited and anxious. I am looking to make the most of this and hopefully is the beginning of something great.

My business offers online marketing and content services for startups, entrepreneurs and existing businesses. However, I have been working hard on growing my personal brand by helping entrepreneurs, startups and small businesses with the information they need to take it to the next level.

I work remotely. At home, a coffee shop, a friend’s place, or wherever there’s wifi. This is definitely not what I thought I would be doing when I was a 12, but then again I was gonna be a lawyer… lol.

I just know I couldn’t be happier, well maybe. There’s always room for more.

I look forward to building the audience I thought I wanted when pursuing to become a professor or teacher. Or the audience I had as a musician.

Also fulfilling my want to help people through podcasts, blogs, videos and meaningful content rather than classrooms and textbooks.

I love helping people, giving advice, seeing others take that advice and do something with it that will benefit themselves and their businesses.

Reading through all this again after writing it has made me cringe a few times, especially considering how irrelevant I believe our educaiton to be (and I wanted to be a part of it).

My parents have done nothing but support me in whatever it is I wanted to do (all 19 career changes), but there was always the traditional idealogy of going to university and getting a “real job” with a great six figure salary. The action of doing or potentially doing that has never seemed to satisfy me throughout my life so far.

This is the short version of my ever-changing road, but I like to think others’ are much longer. I also like to think that this is common, and if you are going to change something in your life, do it while you can, while you can afford it, before you feel a real need to become dependent on your job.

Finally, remember that no matter how many autobiographies, biographies, business plans, how to articles, personal blogs, or whatever else you read, there is no single way to become or be an entrepreneur. You just need to do what you believe in and consistently work hard at it

As Gary Vaynerchuk would say, be patient.

Here’s A Recap (With Some I Pursued But Didn’t Mention):

Musician, singer, writer, actor, model, real estate, lawyer, philosopher, professor, psychologist, teacher, human resources generalist, graphic designer, photographer, web designer, videographer, foodie, restaurant owner, blogger, social worker and entrepreneur.

Questions? Can you relate?

I WANT TO HEAR YOUR STORY!

Shoot me a tweet, Snapchat me, email me, or just leave a comment and I’ll respond back with an answer.

@yolevski on Snapchat

Alexander Yolevski | Founder Yolevski Creative Media

Let’s get in touch @yolevski

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Email: alexander@yolevski.com