Supporting Passions and Paying Your Bills


I love talking about money. I do it for a living. I spend countless hours discussing investments and economics and all things related to wealth. And, throughout it all, I maintain that money isn’t all that important.

Don’t get me wrong, I know money has absurd, even obscene importance; we have to earn it to stay alive, and we spend most of our adult lives thinking about how to bring in more revenue. However, it’s what we do with the money that actually matters. The role money plays in your life depends on what wealth means to you, and what really makes you happy. Holding green pictures of dead presidents isn’t really the end game for people’s happiness.

If achieving your dreams was as simple as separating your real passions from earning income, we’d all be sleepwalking full time. Unfortunately, making a living often gets in the way of living our best lives. We’re constantly told not to follow our passions because it’s not practical; we give up on wonderful hobbies because they cost too much; we talk our loved ones out of doing anything that might not lead to immediate financial returns.

As someone who deals with finances nonstop, I implore you to find a balance. I want you to save and invest and prepare for the future, but if you do so at the expense of all the other joys life has to offer, you need to find a new approach.

While I’m asking favors, I’d also encourage you to support those around you as they try to find activities and outlets they’re passionate about. It’s really hard to pursue something when you feel judged or shamed by friends and family. I’m not suggesting you blindly support bad habits, but you should at least give the benefit of the doubt from time to time.

For now, let’s focus on you. If you’re struggling to find that middle ground between living your dreams and paying rent, I want to help you get back on track. It won’t be easy and there will be days when you want to quit everything, work and hobbies alike. However, if you keep a few things in mind and don’t let the struggles overwhelm you, the money will come while you discover the things that really make you happy.

Skill Assessment

For many of us, the struggle to find a job we enjoy stems from a misconception of what we do well. Until you get paid and receive validation for something, it can be hard to know whether or not you’re an above-average talent.

At the same time, people frequently pursue the wrong thing indefinitely because they never take the time to self-assess. Every once in a while, people just sign up for the wrong passion. Now, this is a fine line to walk, as plenty of brilliant performers and professionals don’t hit their stride until they’ve spent decades treading water and being told to find a real job. This is why it’s so important to be honest with yourself when it comes to what you want to do and what you’re willing to work for.

It’s easy to feel inspired by results other people have achieved. Most of us look at the glamorous life of a billionaire business tycoon and think, “I want that.” If you want that life, you need to have the drive and dedication it takes to get there. Some people don’t have the skills necessary to scrape loans together, live through the uncertainty of launching a startup, work 100-hour weeks and drop everything when business matters arise. Personally, that doesn’t sound like a particularly fulfilling life.

For those of you who have that specific drive, keep dreaming big. When people tell you starting a business is impossible, tune them out. If you can work eight hours in an office and then go work eight more hours on your business plan, you probably have what it takes and you shouldn’t quit.

If you just want the lifestyle and don’t want to do the work, it’s time to look for different outlets. Performing with a rock band in front of a packed arena might sound fun, but it’s not going to happen if you hate the idea of practicing your guitar. If you want people to take your passion seriously, you need to prove you have the drive. Don’t ask people to believe in you – show them why they should.

Find Your Balance

Deciding you have a certain skill set won’t translate to immediate earnings, unfortunately. When you have an idea of what makes you happy, that can give you focus and clarity, but money still needs to be made. This is the hardest part for most people – finding a job that pays enough and doesn’t take 100% of your time and energy.

Some people are wired to work Career A from 9-5, then flip a switch and pursue Career B until midnight. As brutal as it sounds, that’s the path lots of successful people have taken. Maybe the only thing standing between you and your passionate pursuit is a downpayment, in which case working long hours to save money is the best option.

For everyone who feels like their current job keeps them from greener pastures, this is another area where your skill assessment comes into play. What is it that makes you qualified to chase a dream in earnest? Incredible organization skills? Brilliant computing abilities? The kind of brain that can churn out hundreds of fantasy novels? Time to see how you can put those abilities to work in a way that might not be your dream job, but could at least take you a step closer.

Most famous actors were in commercials before hitting it big. Lots of novelists wrote movie reviews for local newspapers before their books got published. A vast number of CEOs started answering phones or working in a mailroom en route to becoming the figurehead of an enterprise. You won’t be able to predict your exact path, but you can definitely try to figure out your starting position.

Balancing professional needs and exciting pursuits requires a long-term plan. You should have big goals and lofty dreams, but you can’t skip any of the steps that might get you there. Don’t look for the quickest route, because that’s usually more of a gamble than a plan.

Try putting equal thought into your paycheck and your passion. If you give attention to both and maintain a responsible approach, you’ll have a better shot at finding a comfortable place in between. With both aspects of your life in mind, the two might start to blend; just by trying to find a balance between a regular job and your bigger dreams, you might surprise yourself and create a career you love but hadn’t even thought about.

Explore Your Options

Without some concrete options for turning a fleeting passion into something bigger, it’s hard to make any movement. If you know your skills, have the drive and just can’t figure out where to start, here are some potential beginning points that won’t force you to completely upend your life.

1. Volunteer

I know, we’re talking about ways to make a living while chasing your dreams and I’m over here telling you to give away your time for free. Is this the very best option? Maybe not, but it’s infinitely better than doing nothing.

No matter what your dream is, there’s a way to surround yourself with people who might support it. From book clubs to activist groups, you can make a lot of headway by donating a little bit of time. And, as we’ve established, you better be willing to sacrifice a few hours here and there if you want to make progress.

There are organizations around the country where people work full time to promote causes they feel passionately about, and most of those enterprises got started because someone was willing to do some work for free. Once that effort picked up momentum, people started paying attention and then the money followed. You can make a living doing something you’re passionate about, but you can’t put the cart before the horse – you need to make the effort before you’ll make the money.

2. Freelance

People spend a lot of time scrolling through job posting sites in hopes of finding a listing that essentially says “DREAM JOB.” Let’s pretend you do actually find such a posting; how big do you think that applicant pool will be?

Rarely do fulfilling careers fall into people’s laps. More often, someone will take on projects because they love the work, find a few clients and put in lots of effort until, low and behold, they’re successful. If you’re struggling to find an outlet for a passion or specific hobby, stop searching on Craigslist and start looking for ways you can do the work yourself.

Freelance work isn’t for everyone, but it can be the best option for someone who needs to transition from one career into something they like better. A brief stint in the world of self-employment is also one of the best ways to find that dream job that never popped up when you were searching online; after you get started as an independent contractor and build your resume a little, your chances of getting hired by a company you like go way, way up.

Freelancers virtually never step directly into the career they’ve always wanted. Hours will be long, work will be hard, pay will probably be low. Fortunately, none of that will bother you as you’ll be taking steps toward doing work you’re passionate about. The long hours will fly by and the measly pay will excite you, as you earned the money through the direct pursuit of your dreams. Right?

3. Bother People… Kindly

You know who stays at a job they don’t like while watching others set and achieve goals? The person who keeps to themselves and never talks about what he or she wants. If you aren’t going to be proactive and vocal about your aspirations, you’ll have a hard time getting things done.

We all need help in achieving our goals. Sometimes it’s a series of small favors, other times you’ll need a friend to go out on a limb and stake their name on your reputation. Whether the assistance is minimal or monumental, you won’t come by it unless you open yourself up to receiving help from others.

Lots of people want to manage every aspect of a pursuit so they can take full credit for anything accomplished. There’s something to be said for taking charge, but think of it this way – would you rather take all the credit for a decent accomplishment, or share the applause after doing something great? If you subscribe to the latter philosophy, it should be easier to pick up the phone and make a call when you need a favor.

I rely on the kindness of others for many things in life, and then I make sure to pay it back as soon as I’m able. I can’t really think of a better, more human way to get things done. There’s definitely a line that can be crossed when you ask too much of someone, but hopefully your friends and colleagues will let you know before that happens.

Talk to people. Ask for advice and learn from those who have what you want. Don’t succumb to jealous discussions behind closed doors; pick up the phone or send an email and find people who can lend a hand in making your dreams come true.

Be Generous

Anyone hoping to follow their passion while still holding down a job needs to be gracious and generous with themselves. You can’t expect to get everything right on the first try, so you need to leave yourself some room for error and expect mistakes. You also need to be generous with how you support your new vocation, and find ways to cut spending in other areas of your life to support your bigger goals.

This is also where you need to be generous in how you deal with other people’s passions and dreams. It’s tough to throw yourself into a project, to commit to something when the odds aren’t necessarily in your favor. A lot of self-doubt comes with setting big goals, so it’s hard enough without having other people offering their doubts on top of your own.

From the reverse perspective, I understand wanting to hold someone accountable. It’s one thing to have a passion; it’s entirely different to pursue it. If someone is talking about big plans but not taking any action, they may need a little kick in the pants. Conversely, if your spouse is giving their all and living through a string of failures and rejection, they deserve a little bit of support.

In those early days of trying to do what you love, when your mind is on something great while your time is spent trying to make a living wage, the balance is incredibly tricky. It feels like all aspects of your life are volatile, and if you make one wrong move everything will come crashing down.

The normal response is to retreat into the safety of your day job, making sure you can at least buy food. Sometimes that’s the responsible thing to do, but that doesn’t mean you have to stop setting goals and thinking about ways to reach them. If you really want it, you’ll find a way to make it work.

If you take one thing away from this post, it’s that you can – and should – start small. Go to a meeting, read a book, send an email. Your dream career isn’t going to sweep you away from your current job before you put things in motion and make some headway. By taking action, you chip away at the wall between you and whatever it is you’re pursuing. Each small step gets you closer, and when you finally have those big goals within your sights, it becomes much easier to make big, life-changing moves.

It all starts with looking for a balance. Ignore the money for a quick second while you think about what you really want. When you know what you’re aiming for, think about how you can pay your bills without losing sight of your dreams. Keep both objectives in mind, adjust your efforts accordingly, and you’ll be on your way to living a life that really makes you happy.

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