Is Finding Your Own Way to Success a Struggle for You?

I was reading an article today in Pen World Magazine, “From Cyberspace to the Real World” (April 2015 issue). It is about a blog, The Pen Addict, and how it gave birth to a business and has inspired a new generation of pen lovers — including me.

In the article, there is a paragraph describing Brad Dowdy, the founder of The Pen Addict.

Perhaps typical for his generation, he meandered a bit before he found his true passion. Sometime along the way, while earning a degree in music, business management, doing a stint as a professional golf player, and working 15 years in the technology industry, Dowdy noticed that the tactile experience of putting pen to paper is incomparable to tapping something out on a keyboard – and far more satisfying.

I tripped reading that sentence. Perhaps typical for his generation, he meandered a bit before he found his true passion.

Perhaps typical for his generation…

Is it truly typical of his generation? Are we making this generation out to be lost souls who have to meander a bit before finding their way?

Or are we the first generation who feel that we are allowed to change course if we are unhappy?

When I graduated from high school in 1987, I felt like the expectation for my future, the success path that I was supposed to follow, was to go to college, get a degree, and get a job with a company that I would then stay with for the next 40+ years until I retired.

I did not follow this path.

I never finished my college degree, and I’ve beaten myself up over it for the past 25+ years. It has always loomed over me as a symbol of failure, of not being good enough.

I have job hopped my entire life. I’ve babysat, worked as a hostess, a grocery store cashier, at a photo agency that photographed marathons and Party Pics, I scooped ice cream, waited tables. I went to college the first time, straight out of high school, thinking I wanted to be a teacher. Instead of finishing my degree, I got married to my ex-husband and moved to Germany.

When I returned to the states, after my divorce, I worked as a receptionist, a litigation support coordinator, a database administrator, I made soap full time, and I was an incredibly successful digital strategist / salesperson for two web design firms. I then owned a blog hosting company.

I sold the hosting company when returned to college in my 30s, intending to go to pharmacy school – until I realized that all I wanted to do was take pretty pictures. (It might have been a particularly stressful semester involving Organic Chemistry.) I was a professional wedding photographer, and am now working as a business coach as I build the Wedding Professional Association.

Yes, you could say that I’ve meandered.

I feel like there has been a major cultural shift that has happened in the past 15 years. When I was a child it seems as though you were not allowed to change jobs, to change the work that you did unless you were moving up the ladder. You stayed with the same company for life, and it was rare if you changed. It felt to me as if it was frowned upon, that you whispered wondering what happened if someone switched employers.

Then in the dot com era, it all changed.

People started to move around, to shift companies as needed – or as they desired.

Sometimes for money, sometimes to advance their careers, sometimes because in the moving sands of the dot com era your company was just gone one day.

This was the first time that the conversation of “finding your passion” began to really be a thing, especially working on what you were passionate about. That you might leave a job, completely change what you do, because you wanted to follow a dream.

No longer a hobby, your passion was also your job.

Is that a bad thing?

I struggle with this. When I list out all the jobs I’ve ever had, I feel embarrassed. Like I’m a flake. A failure.

The reality is that that isn’t true — that every job has taught me a variety of things along the way that I still use in my life. I learned in the late 1990s how to be a “geek translator” and I still use that almost daily. I sold my hosting company for a profit – I’m a dot com success story. I earned six figures every year as a professional photographer, thanks to my knowledge of the internet & marketing online that I learned in those early dot com years.

Yet still, reading that line, “Perhaps typical for his generation, he meandered a bit before he found his true passion” bothers me.

Is it that I think that meandering is a negative trait?

Is it labeling his generation (my generation) as meandering?

Is it because we, as a generation, have had the audacity to feel that it is better to do work that you’re passionate about instead of following the path we are told we should be taking?

Do we need to shift our perspective of what success looks like as a culture? To celebrate this journey that many of us seem to be on?

Or do I live in a tech bubble where this journey seems to be the norm — and it isn’t like that for most of the world?

I feel as though I’m caught in the tide of progress, that for 30 years I’ve been pushed and pulled – encouraged to seek my own path, the one that is success for myself, and yet also expected to follow that cultural norm of getting the degree, the good job, the solid career.

I’ve reinvented myself countless times. I’ll most likely continue to do so over the remainder of my life. There is always a common thread through it all – the desire to learn more, to explore. To teach others, to help them be more confident. To seek the beauty of stories, and to share them with others.

No, I do not have a college degree. I don’t know if I’ll ever return to get one, I don’t know that that will ever be the path for me to take at this point.

Perhaps typical for my generation, I’m learning to accept that I’ve found success by creating my own way.