Not Career Advice is a monthly podcast and a̶d̶v̶i̶c̶e̶ coaching column that asks and answers questions about "making it" in your career—and what that even means.
You can submit your own question here.
The career question
Hi Taylor! Firstly, I love your Inner Workout book. It’s one of my favourites. I even requested that my local library in Australia order a few copies so more people could enjoy it. Thanks for offering the opportunity to submit a question.
I’m in a period of transition in my business; a ‘pivot’ to quote Ross Gellar. I’ve been a virtual assistant for multiple years, and in that time, I’ve well-and-truly outgrown it. But I feel stuck in this sense of fear around expanding from the business comfort zone I’ve created for myself like it’s easier to hide IN other people’s businesses than to put myself in the spotlight (which I know ties back to childhood self-esteem issues, being picked on, wanting to hide and not show myself). It also feels like starting again, not taking a wage for a while as I build my skillset in a particular area (design).
Anyway, an opportunity landed in my direction recently, like the Universe was saying a huge, ‘Here’s your opportunity, take it, go down this new path and follow your dreams!’ but that voice in my head is still saying you’re not good enough, you can’t do this and I worry so much about what people will think, especially those who follow me on Instagram, like, “oh, so she failed at business, now she has to start all over again.” whereas it feels more an evolution yet I still have this sense I need to justify my choices to strangers? Yet I don’t know why... What advice can you give me to push through the self-doubts?
- Sarah
The not career advice
Sarah,
Well now, I’m blushing. Thank you for sharing the Inner Workout book and for this note.
If we were in a session, I’d invite you to take a few deep breaths and offer you my most reassuring smile.
The first thing I want to do is to celebrate with you. You did the thing! You built a business and a skillset as a virtual assistant to the point of mastery.
Have you allowed yourself to feel proud of that accomplishment? And I mean proud without any asterisks about how much money the business should’ve made or how many clients you should’ve had or any of the other shoulds that often get in the way of us acknowledging our accomplishments. What would it look like to celebrate?
Beyond celebration, your letter made me curious. It sounds like you view your options as: continue VAing or transition into design—without taking pay. Are those really your only options?
Maybe I’m reading too much into a throwaway line, and you’re fine to go without pay for a season. But if any of your shakiness around taking this leap is financial, I’d encourage you to brainstorm third options. Do you have to tell people about your transition right away? Do you have to stop VAing now as you learn design? What’s the and option? How can you make money and develop your design skills?
Which brings us to the heart of the matter. You said you feel the need to justify this decision to strangers. Do any strangers specifically come to mind? If so, how much do you value their opinion?
I’ve done versions of this reflection myself only to realize that I was basing a decision on the opinion of a college classmate who I haven’t talked to in years.
But, more frequently, the judgments I’m afraid “they” will make are the ways I’m currently judging myself.
Be honest: do you feel you’ve failed? How do you define success and failure in your business and career?
And finally, speaking from my pivot-filled career experience, people might enjoy seeing your evolution. I’m sure some folks are put off by the way my career’s evolved, but no one’s ever sent me a note saying that. I have, however, gotten notes saying that my career evolution and pivots have expanded people’s idea of what’s possible.
Trust yourself, Sarah. Trust your desire to pivot. Trust that the right people will follow along into whatever’s next for you, and that there are even more people waiting to meet you in your next career evolution.
- Taylor
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