Blogger Jackie Lam lays out a game plan for turning the idea of a dream job into reality.

If you could pursue your dream job tomorrow, what would you do? What would you need to get there? Maybe you’ve always wanted to move out to the country and run an alpaca farm, or make a go at selling your unique handmade wares on Etsy. While you might be tempted to quit your job tomorrow and dive into your pursuits full throttle, it’s best to make preparations before making your first move.

Here are some questions to ask yourself to make sure you can truly afford your dream job.

What’s Your Game Plan?

First off, you’ll need to carve a path toward your dream job. What will you need to do to get there? What are the steps you’ll need to take, and what’s your time frame? Spend some time carving out a plan, and think about the specifics of your game plan. Maybe you’ll need to work part-time at your job, moonlight, or take some time off altogether to go back to school. The more fleshed out your plan is, the easier it will be to visualize how exactly you’ll get there.

What Are You Willing to Sacrifice?

If you have a family and you’ll be busy moonlighting, would that mean spending less time with your kids? Would socializing with friends turn into rare occurrences? Or maybe you’ll need to take some time off work and will have to put your long-term goals, such as retirement or saving for your first home, on the backburner. Ask yourself: Is the trade-off worth it? Making a list of pros and cons will help you figure out if it’s the right decision.

Do You Have Enough Saved?

No matter what your future pursuits are, if you plan on working less to focus on your dream job, you’ll need the wherewithal to squeak by. So, how much is enough? Some say $10,000, while others say six months of basic living expenses. An exact amount can be tricky. There is no one-size-fits-all number, and it depends on what you’re comfortable with and your personal needs.

While making the transition to full-time freelance work last year, I had saved enough money to compensate lost wages, and I was raking in roughly half of what I was making working my full-time job. I’m inherently risk averse when it comes to my finances—while some folks might be comfortable having three or six months worth of wages in their rainy-day fund, I needed 12 months’ worth to feel secure enough to pursue freelancing.

Can You Handle More Debt?

If your dream job requires that you go back to school or have some seed money to jump-start your business, you might need to take on some debt to make your dream job happen. Before you make this decision, if you have existing debt, see if there’s anything you can do to either postpone or lower your current payments. Depending on your situation, you might be able to request a forbearance or deferment on your student loans. You can also reach out to credit card companies to see if you’re eligible for a lowered interest rate, or see if transferring your balance to another card is worthwhile.

If you’re not comfortable with taking on more debt, look into alternatives or modify your game plan slightly. Maybe you can side hustle to earn some quick cash or find ways to scale back on your living expenses.

Do You Have a Backup Plan?

Your backup plan doesn’t necessarily have to be drastically different from your current goals. You don’t have to go back to your old job and admit defeat, but it could be a series of slight adjustments.

As a freelance writer, if I don’t end up landing work with a client I’m interested in working with, I have a list of other customers in my periphery to contact. If I ever find that I don’t have enough freelance writing clients, I scour the Internet for other writing opportunities—sometimes outside of my preferred specialties. I’ll also take on a side gig or two that don’t involve writing to supplement my income.

Are You Prepared for the Transition?

While you wish to land your dream job overnight, an in-between period from where you’re at and where you want to be is inevitable. It took me about a year from the time I plotted an escape route into freelancing and when I found the opportunity to do it.

A good friend told me that taking the big leap is enduring the last few steps where there’s a scary gap or dicey precipice that you need to traverse. Don’t panic! The hardest part of any transition is dealing with the unknowns, and risk is an inherent part of running down a dream.

No matter how prepared you are to pursue your dream job, you’ll have to face your doubts and insecurities. It’s difficult to put a price on peace of mind, but asking yourself these questions and having securities in place will ensure you can do what you want.


Jackie Lam is the creator of Cheapsters,
where she helps freelancers get by in the gig economy.
She lives in L.A., where she is on the perpetual hunt
for the perfect breakfast burrito.

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