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10 Tips to Help You Quit Your Day Job and Pursue Your Dream

You've heard the saying: "Failing to plan is planning to fail." These strategies can help you ensure a successful transition to the career of your dreams.

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Figure out how much money you need to get your business off the ground

As a career coach, I often have a client to come to me with a great idea for a business that they can run from the comfort of their own home. Maybe it’s an interior design business, a tutoring business, or a catering business. My first question: “How much money are you planning to spend on this venture?” Do you need a website, business cards, a dedicated home office? Might you need to go back to school? Figure out what you’re prepared to invest in your dream job in order to make the money you want to earn. Have a budget and financial plan; don’t just close your eyes and hope. Here are some tips to help you look for a job while you still have one.

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Find a transition job to make money while you’re ramping up

After you quit your day job, you’ll need a steady income while you’re figuring out how to start your own business. My clients will take simple jobs where they can clock in, clock out, and collect a paycheck. The most popular roles are servers or bartenders; this is the transition job of choice for thousands of actors in New York and LA for good reason!

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Get your partner on board

I’ve noticed a common link with the guests on my radio show, Find My Thrive. All the people who have made significant life transitions to pursue their dreams have a person in their life who says, “Honey, go for it. You’re good at this, and you can do this,” and then helps that person tackle obstacles along the way. Whether it’s someone with a deep passion for yoga who wants to teach at a high level, a singer who wants to start her own band, or a 9-to-5-er who wants to be a voice over actor, a key to their success was having a supportive partner who encouraged them to go for it.

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Be sure you can say “yes” to the most important career question there is

When it comes right down to it, everyone who comes through my office wants the same thing: to make a meaningful contribution. They want to use their skills, abilities, interests, and talents to make the world a better place. I know you want to quit your day job, but does your dream job help you make a meaningful contribution?

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Have more than one income stream

This is the slash economy! These days my baker is a florist, my babysitter is a house painter, and most teachers I know also tutor in the summer. Everyone has a side hustle, whether it’s the journalist who is a ghostwriter for newsletters or the yoga teacher who can help you with your taxes. Don’t bet the house on just one thing; figure out a couple things you can do. Here are some quick ways to earn extra cash.

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Don’t confuse a hobby with a dream job

This one is really important. When I applied to culinary school, the most famous school of them all, the Culinary Institute of America, required that every applicant spend six months working in a restaurant, bakery, or some type of culinary venue. Why? They wanted to make sure you weren’t wasting your time or money on what was less a job than just a hobby that you enjoyed. Is this dream that you’re pursuing something that you enjoy doing for fun or can you stand the actual work you’ll have to do to make a living? There’s no better way to take the pleasure out of a hobby than to turn it into a revenue source.

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Talk to people who do the job you want to do

I receive at least one phone call a week from people who would like an “informational interview.” I always give them the time, twice as much time if they buy me a coffee. If you think you want to make a pivot, do your research—ask people who’ve done it: What do they like about their job? What don’t they like? These people can show you how to get closer to your dream job. And remember the golden rule about informational interviews: Keep in touch! If someone has been generous with their time, let them know how it turns out for you. After all, these people will be your first friends in your new field. These are the networking tips you’ll need to land your dream job.

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Don’t “take a leap of faith,” but a calculated risk

Many of my clients are under the misconception that if they were “just brave enough” they would take that big leap. I completely disagree. You’re taking a risk, and all change is risky, but then again, so is standing still. Spend the time to figure out if this could work—do you have the skills for the new job, or do you have the discipline to obtain them? Will you be able to make the money you need to support your lifestyle? When you talk it through, does changing careers make sense? Can you explain your dream to other people and do they “get it?” If it seems too scary, there’s probably good reason for that.

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If you’re getting cold feet, write out a vision of your future that feels right

I have a client who knows that she is leaving her job within the next six months; it’s just a question of exactly when. She’s financially secure, but is working 60 hours a week in a job she hates. So I gave her this challenge: “Tell me how you want to spend your summer. Would you like to travel, see family, and play at the beach?” I asked her to write me a description of her ideal summer. By creating a vision for a better future, you can help yourself make it so. Here are the signs that you could be in the wrong career.

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Work with a partner who keeps you accountable

I’m a life and career coach, so I help people figure out how to get their dream job for a living. People pay a fair amount of money to work with me, so that I can help them design their future, hold them accountable as they move forward, and ultimately reach their goal. You can find a coach to work with, or you can find a friend, a colleague, or a mentor to walk down this path with you. Connect on a regular basis; commit to weekly goals to move toward your dream job, and have them hold you to it.

Allison Task
Allison Task is a certified Career & Life Coach in Montclair, NJ. She helps people thrive. When not at work she's keeping her head above water with her 4 year old twin boys, 3 year old daughter, 15 year old stepdaughter and too many goldfish. She also hosts the Find My Thrive radio show and podcast that can be found on iTunes or www.findmythrive.com. For more, please visit www.allisontask.com.