Why You’re Still Clinging to Your “Shadow” Career

Your shadow career is a safety blanket but you have to learn to let it go if you want to follow your true calling

Marguerite Faure
The Startup
7 min readJun 12, 2021

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Photo by XPS on Unsplash

Steven Pressfield introduced me to the concept of a shadow career:

“Sometimes, when we’re terrified of embracing our true calling, we’ll pursue a shadow calling instead. The shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.”

Here are examples of shadow careers that may be relatable to some people:

  • An actor or director at heart decides on becoming an entertainment lawyer.
  • An aspiring author hides behind the daily grind of writing content for companies.
  • A passionate musician procrastinates writing their own music and chooses to take the route of being a wedding singer.

It’s so close to the true calling, but we decide to avoid what is needed to step up to where we are being creatively pulled.

I’ve been marinating in this uncomfortable space for a few months now and, even though I feel a tsunami of overwhelm:

I’m resigning from my second shadow career tomorrow.

Here is some context…

I entered one too many reality TV shows in high school hoping for an acting break, only to end my schooling career with an examiner pulling me to the side, “Get a degree in business, make some money- and then, write your own shows.”

So, I got a degree in marketing, while working full time, and, after switching between six different marketing and sales positions, between the ages of 18 and 26, I quit my corporate life and started my next phase of a shadow career: Online Teaching.

We’re encouraged to take bigger risks while you’re young, and even though I took a step away from the line of work that put a lid on my personal passions, I entered another shadow career.

I convinced myself online teaching had the potential to be a stable source of income while I explore film and screenwriting.

It was.

In my first month as a teacher, I wrote my first full-length screenplay and submitted it to an international screenwriting competition.

It bombed.

It took me a year and a half before I had the courage to write another- which got an astounding 88% and a review that read, “You may well have interest from multiple buyers and assorted A-list talent.”

But, I never won the competition, and after emailing over 100 agencies, I still couldn’t find an agent.

I needed to consider a change in approach, but feeling sorry for myself paused my journey.

It took three and a half years before I had the courage to start a serious YouTube channel.

The goal was that I need to become proficient in the aspects required to function independently in the movie business. This meant that I had to take ownership of scripting, editing, acting, directing, and producing my own videos.

I’m 1.5 years into YouTube and I’m making enough money from Adsense, sponsored content, and affiliate marketing, not to teach, but I haven’t had the courage to quit.

I’ve once heard Steven Pressfield say, “Get your ass where your heart wants to be.”

Well, I’m publically trying to be a less-talk-more-action kind of girl- so, here it goes…

I will probably ball my eyes out when I do it, but if you’re too afraid to leave your shadow career, here are the reasons I’m terrified to leave mine.

Softener #1- It’s not that bad

I’ve had far too many friends stay in relationships that are dead, just because they fear being alone.

The opportunity cost involved with stepping out of something average sometimes doesn’t meet the energy required to start from scratch.

Being stuck-in-a-rut is like comfort food.

In my case, the corporate world was an obvious mismatch in terms of fit.

However, the shadow career of online teaching wasn’t a nightmare.

In fact, it had many moments where it was a dream come true.

It provided me with autonomy and, because I taught children in China, I was able to connect with and learn about a different culture.

Some of the children came from homes where there was enormous pressure to constantly perform, and my classes became a fun space to escape.

Unleashing my own child-like spirit, while watching a child step into theirs while learning, resulted in me feeling blessed to impact the next generation.

But, I knew I was using this job as a delicious dose of procrastination.

The takeaway here is to reflect on whether we are being true to ourselves.

Malcolm Gladwell writes about the three requirements for fulfillment in Outliers:

1. Complexity

Is the work you are doing challenging you?

Coming out the other side of a complex situation results in us experiencing a sense of reward, or accomplishment on completion of the project.

2. Autonomy

I’m sure I speak for all of us when I say that no one likes to be mico-managed.

The freedom to think independently is a contributing factor to self-motivation.

3. Accountability

This is where you determine the correlation between effort and reward.

In my case, I knew that I wasn’t being mentally stimulated. Not that teaching isn’t difficult, believe me, teachers do not get enough credit for what they do.

But personally speaking, I knew I was not working on, or growing my skills as a screenwriter or director which have been my desired journey for the longest time.

I also had a gut feeling that I was the only person to blame if I never gave it a proper shot.

I was fearful of breaking out and entering a world full of learning curves. I wasn’t completely fulfilled with online teaching, but I had enough.

I felt greedy for wanting more especially because what I had wasn’t bad.

Softener #2- Fear of letting go

I’m sure you can relate to the pain of loss.

Stepping to the side, and losing part of what feels like your identity requires some space for mourning.

We all handle situations differently, but I get headaches and feel sick when I need to move from one season in life to the next.

In the first few years, online teaching was the financial springboard I needed to create space for actioning projects I was passionate about.

It provided me space, time, and financial support I needed to work on what I really wanted to do.

However, this year, I’ve only been teaching between 2 to 5 hours a week and so there is really no financial benefit in staying.

Honestly, I’m afraid that if I quit, I will lose my lifeline.

I used the analogy of a relationship earlier on, and it feels like I am breaking hearts. My heart is one of them.

I know people will forget about me and move on. But, I’ve watched shy kids turn into karaoke kings and queens. I’ve also observed the incredible transformation from someone not being able to read- to answering comprehensions perfectly.

I’ve built relationships with managers and grown a love for Chinese festivals and celebrations.

I’m struggling with the idea of letting go- even though it makes no sense from a time or financial perspective.

But that’s the problem with these shadow careers. There’s this fear of moving on because it hits so many of the beats that we’re after.

I’ve never had to dig so deep to identify what I truly want.

I’ve also never prepared this hard to say goodbye to something.

3. Fear of being serious

If you have a shadow career, it’s probably a safe bet.

Parents, friendships, and communities can be somewhat judgmental if someone is changing a dynamic.

A hobby is fine, but when you want to grow and challenge who you are in the eyes of those around you- you may be hit with a deadly dose of negativity.

Personally, I’ve shared with very few people that I’ve been creating content on YouTube.

Most people in my life think I’m a full-time online English teacher.

I’ve loved being boxed this way.

With no one being able to judge my dream, I’ve been able to maintain a somewhat healthy relationship with making videos.

I’ve spent a year and a half learning how to create content on YouTube which is a giant step in the right direction- but I’ve been too afraid to try to create my own films.

I’ve had a shot in the dark in some attempts of “short films” but I’ve been creating YouTuber-type content as opposed to getting my hands dirty and filming films.

I’ve told myself that I don’t have the time to focus on bigger projects because my plate is too full, also, with so many hats- there has been more than enough to learn.

For me currently, getting a video up once a week has been good enough.

I get to maintain a life that I know while I dabble in a world that speaks to my heart.

Not quitting teaching has become a softener in terms of how I allocate my time.

My experience in the film industry is comparable to being invisible. However, YouTube has given me a platform where there are no excuses.

If I make something worth watching, there is a chance that someone will watch it.

But not having something to blame anymore, requires that I take full ownership.

I have to turn professional.

Final Thoughts

The effect of not following your true calling affects us all differently, but here are some of my observations so far.

I’ve seen parents try to live their dreams through their children. I’ve seen a spouse trying to live their dream through their partner. I’ve watched people build resentment or live in a time period where they were close to their personal best.

I think it is fair to have a shadow career while you are becoming financially stable.

But, there comes a time when you’re making excuses and, even though you’re trying to reason with yourself, you become aware that you’re your biggest stumbling block.

If you’re in a space where you’re clinging to a shadow career, I hope this piece of writing has given you an interesting perspective on why it’s painful to let go.

I can’t write an entire article about why it’s terrifying to step further into a direction that I wholeheartedly desire, and let fear kill my dream.

So hold me accountable.

This jump makes me nauseous but I’m about to Peter Pann this shit and lose my shadow.

Wish me luck.

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