5 Tips for Dealing with the Reality of Your Dream Job

UPDATED: May 7, 2024
PUBLISHED: June 21, 2021
5 Tips for Dealing with the Reality of Your Dream Job

Following your dream sounds like a fairy tale. But the road to happily ever after never did run smooth.

Fashion designer Rebecca Minkoff’s Cinderella story started not with a glass slipper but with a dress. After her mom—the fairy godmother in this story—taught her how to make a dress she’d seen and desperately wanted, Rebecca knew fashion design was her path.

It wasn’t easy. She was forced to pivot early on, and the competitiveness in the industry—even between women—was suffocating.

Today, in addition to her famous fashion brand, Rebecca hosts the podcast Superwomen with Rebecca Minkoff, and has released her first book: Fearless: The New Rules for Unlocking Creativity, Courage, and Success.

“We all have fear, and a lot of us let it stop us,” she says. “How do we adopt new rules and new ways of behaving that allow us to say, ‘I’m scared, but I’m gonna do it anyway.’”

In this episode of SUCCESS Stories, Rebecca tells Chief Storytelling Officer Kindra Hall about what it really means to be fearless, the kinds of questions people should be asking industry leaders, and her unexpected strategy for dealing with burnout (hint: it’s not a scented candle.)

Being fearless doesn’t mean never being afraid.

You can’t stop yourself from feeling scared sometimes—and you don’t need to. Fear is your brain’s way of warning you about a potential threat. For our ancestors, that meant predators and disease. Today, we feel a similar emotion when we’re approaching our boss for a raise or making a risky business decision.

In these cases, instead of trying to not feel afraid—or feeling guilty when you do—learn to accept the fear and do what you need to do despite its lingering presence. 

Taking scary risks gets harder as you get older and have more responsibilities. If you’re relying on your salary to pay your bills, analyze your situation honestly and plan ahead. Be prepared to spend all your spare time on your side project. Make sure it has real potential to make money, and that there’s a market. Wait to see returns on your investment before you switch to it full time. Being fearless doesn’t mean being reckless.

Know when to pivot.

Four years into Rebecca’s first apparel collection, she realized it wasn’t making any money. However, her first bag (known as the Morning After Bag or M.A.B.) became an instant hit. 

Instead of doubling down on the apparel line, Rebecca let the market lead her. She closed down the clothing side and focused on becoming a bag designer.

“I didn’t give up: we had to pivot to the thing that was going to pay the bills, and show us the greatest leap forward as a company,” Rebecca says. Pivoting means understanding where you’re most successful, even if it’s not where you originally expected and capitalizing on that momentum. Don’t be too stubborn to learn from your customers.

Support your rivals.

As anyone who has ever played or been banned from Monopoly knows, everyone gets competitive. But instead of letting that instinct lead you into a stop-at-nothing war with your rivals, it benefits you to work together against shared obstacles.

For example, Rebecca observed two unique problems facing women working in fashion:

  1. Many women with power were reluctant to help other women, and actively worked against them if it meant further advancement.
  2. There were still glass ceilings preventing women from reaching certain high-level positions.

Rebecca realized that women could overcome these issues if they put their competitiveness to the side and supported each other. She founded the Female Founder Collective to encourage that collaboration.

When you feel competitiveness surging, reach out to the person who has you feeling threatened, and see how you can work together to a mutually beneficial goal. This not only helps you, it also sets a good example for everyone else and promotes a kinder industry.

Be specific when you ask for advice.

Resources like LinkedIn have made it easier than ever to ask people at the top of your industry for help. When you reach out, make your questions as specific as possible. 

Vague questions are difficult to answer concisely, and indicate that you haven’t bothered to do the minimum amount of research. For example, avoid questions like:

  • “Can we get coffee?”
  • “What should I do with my career?”
  • “How do I get started?”

Instead, focus on specifics. For example, in the fashion industry, Rebecca recommends asking things like:

  • “How do I get my sample mass produced?”
  • “Which store should I approach with my collection?”
  • “Can you introduce me to an angel investor?”

These prove that you have a basic knowledge of the industry, and can be answered in a few sentences or bullet points. You’re more likely to get a response, which could be a one-off or the start of a relationship.

If you’re feeling burned out, it’s your work that needs to change.

Face masks and scented candles have their place. But no matter how clean your pores are, or how much your house smells like a field of lavender, if you hate your job, you will still feel worn thin.

Instead of addressing the symptoms of burnout—stress, tiredness, irritability, crying in the office bathroom every Monday—tackle the cause: work. 

  • Look for things in your job that you enjoy. Most people can’t spontaneously quit a job they hate. Instead, look for the aspects you like. Maybe that’s the people you work with, or connecting with customers, or decorating the store window. Focus on those, and try to develop those parts of your job as much as possible.
  • Find joy outside work. If your job is leaving you burned out, find something else you’re passionate about that you can do on the side. It might be volunteering, a hobby or a side job. Feeling fulfilled in that aspect of your life will make it easier to cope when your main job is dragging you down.

People often think that working less is the solution to burnout: but making your work and your life fulfilling will help sustain you better than a facial come Monday morning.

SUCCESS Stories is no longer releasing new episodes on the SUCCESS Podcast Network, but you can still listen to the full conversation below.

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