Live Your Daydream: How to Make a Living Doing What You Love

Things are starting to ramp up over here at Shaner HQ and lately it seems like I've been getting inundated with people asking me for advice on how to make the leap from boring office job to the exciting (and mildly terrifying) world of running your own business.

While I love talking to everyone individually (I'm a huge chatterbox) it seems like a lot of the same questions keep coming up: how can you figure out what to do? How can you get from 9-5 to full-time business owner? What are the challenges along the way? and so on.

So it seems best to address them in the best way I know how: a blog post, of course!

This isn't going to be a bubblegum session where we talk about the magical dream that is running your own business (though it is pretty kickass); today I want to talk to you about the real-life things that you need to do to start doing what you love for a living.

Figure out what you want to do

So you've got a full-time job that doesn't excite you and you know that you want to run your own business instead, but where the heck do you start? First, figure out the thing that excites you the most and focus as much of your time and energy on learning as much about it as you can.

Maybe you love writing and want to be a copywriter, maybe you love building websites and want to help people build websites for their businesses, or maybe you love knitting awesome sweaters for your cat. Who knows. What matters is that you love doing it, it excites you, and you're dedicated to turning that passion into your livelihood.

The best (and safest) way to start working towards your goal of being a full-time businessperson is to start small. Spend a few hours a week honing your craft, reach out and try to get to know influencers and other people who might be able to help you, find a mentor if possible, and try to gather a small roster of clients.

By having a few clients on the side you can safely get a taste for what your full-time work will be like, start to understand the ins and outs of client relationships, and spend some time thinking long and hard about whether or not these experiences are indicative of the kind of lifestyle that you want to have.

Start to plan

So you've spent some time learning, testing the waters, and have decided to make the plunge into the crazy world of running your own business. Good for you! But before you go quitting your 9-5 all willy-nilly, you need get your ducks in a row first.

Take a step back from your life and look critically at where you are: where are you working? Do you like where you work, and how long are you planning to work there? Do you have any debt, and what are your goals for paying it off? What are your basic costs of living? You get the idea.

Next, sit down and prioritize your goals. For me, my biggest goal was to have as much of my Visa and my student debt paid off before I quit as possible. I made the decision to leave my job in December of 2014, and I spent the next several months working full-time, collecting clients on the side, and using the money that I was making as a freelancer to aggressively pay off my debt. Being able to tackle this huge weight gave me some breathing room when I finally started running my business full-time, and I wish I could go back in time and high-five my past self for being so forward-thinking. I really did myself a solid.

So is there something that you'd like to accomplish, or start doing before you start running your own business? It doesn't have to be debt-related; it could be anything from taking that amazing trip, to buying that new laptop, to meeting with a financial advisor. Whatever it is, do your best to do it before you go solo, because you're going to want to hit the ground running.

Now is also the time to start thinking about the details of your business. By having a deep and thought-out understanding of who you are, what you offer, and the kind of business you want to run before you get going full-time will save you a lot of hassle down the line, and will help you stay laser-focused on your goals.

Some questions to ask yourself are:

  • What specific services will I offer?
  • What is my ideal number of clients?
  • How much will I charge for my services?
  • What kinds of contracts do I want to have (eg: recurring, one-time, etc)
  • What is the basic monthly income that I need in order to survive?
  • How will I find new clients? (eg: blogging, online promotion, Meetups, etc)
  • How much money can I save before I quit, and how much runway* will that give me?

*Runway refers to the length of time that your business can exist without collecting any additional sources of income. So, if your client pool dries up, how long until you need to go back to a 9-5.

You get the idea. There are tons of other questions that you'll need to ask yourself that are more specific to your circumstances, but these should get you started.

Treat your goals like recipes

What I mean by this is do everything one step at a time. It can be totally overwhelming to look at all the things that you want to do, or that need to get done, and start to freak out internally because how the hell are you ever going to accomplish all that? By breaking it down, that's how.

Think about your biggest goal and write them down. What do they look like? Do you want to quit your office job by 2016? Be on the cover of your local paper? Land that dream client you've always hoped to work with? Write it all down in as much detail as you can think of.

Now that you've written it down, plot out all the steps that you need to take to achieve that goal and say them out loud as you write them. It sounds cheesy (I know) but it absolutely works. Seeing the words on the page and hearing your own voice saying them helps make those steps seem more real and attainable.

Now that you've set out your goals and broken them down into smaller, attainable steps, it's time to start chipping away at them.

Don't freak out when your plan goes awry

Remember how I said that I had those lofty goals of paying off all my debt before I became a full-time businesswoman? Yeah, that didn't happen. I've made a significant dent, but to quote John Steinbeck: "the best laid plans of mice and men often go awry", and things came to a head at my old job and I had to make an exit before I totally lost my mind. It was a bit sooner than I'd anticipated (by a few months) but by planning ahead and actively working towards this goal for several months beforehand I was in a much better position to start kicking ass and taking names right away.

Remember: just because your plan didn't execute perfectly doesn't mean you fucked up. It means you're human, and it just means that you have one more challenge to face (and overcome!) on your road to independent businessperson fabulousness. Do your best to plan what you can as far in advance as you're able, and when life tosses you a curve ball, you'll be ready to react.

Plan for the best & prepare for the worst.

Be honest with yourself about money

#RealTalk time: running your own business doesn't mean you'll be swimming in giant pools of cash mo-nay immediately. In fact, for most people it takes a long time, sometimes years, to start to really pull in a significant amount of income. Most of us, myself included, take giant pay hits, sacrifice our social lives, travel plans, and long-term goals like home ownership or even having a car because we want our runway to last as long as possible.

(this is an accurate depiction of what running your own business feels like)

If you've been smart and saving up, or you've got a big cash influx from a contract (or both, if you're lucky) for the love of god don't spend it all at once. I know how good it feels to look at your bank account and see all those dolla bills sitting there, but working for yourself is much more precarious than a 9-5. With a regular job you know you have income coming your way every two weeks (or whatever your pay schedule was) because it was on a schedule, so who cares if you spend a bit extra this weekend - you know exactly when the next influx of cash into your bank account is going to be.

Clients don't usually work that way, and it's not uncommon to wait several weeks for a payment, or for contracts dry up overnight. This is why keeping that runway as topped-up as possible is crucial.

Pound the pavement 24/7

I mean it. When you start running your own business the amount of contact that you need to have with other people (aka "exposure") needs to ramp up significantly. If you weren't active on your own blog, social media feeds, and out and about in your city, it's time to start putting yourself out there.

Believe me when I say this: the amount of work that you put into making sure people know who you are will have significant long-term benefits. It might take some time, but if you can start to develop a positive reputation as being "in the know" about your industry, people will start to defer to you, and eventually will start to refer you to others.

Last year I at one of my speaking engagements I mentioned that I'd been blogging for over a decade, and that experience is what helped me land the role I had at the time. I was speaking to first-year Creative Communications students, and one of them asked "why should I keep my profiles updated when I'm not looking for a new job?" My response to the student was "you never know when an opportunity will find you," and to that I'd like to add that when you run your own business you are always looking for a new job. Ideally you'd like to get yourself to a position where you're turning down work, but until you get there (and if you get there) you need to be as active at promoting yourself and your business as possible.

Ignore the haters

Like the old saying goes: haters gonna hate, and I guarantee you that from the second you mention that you're planning to start your own business there will be someone naysaying the idea right from the get-go. It might be a colleague, friend, family member, whoever. They might put down or dismiss your goals, and will likely do so under the guise of "being concerned" and "caring about your well-being." If anyone in your life says that to you, make a point to respond by saying "if you're concerned about my well-being, then help me achieve this goal because it will make me happy."

Remember: what you're doing takes guts and courage, but it's something that anybody can do if they just work hard enough. There will always be reasons and excuses to not pursue your dreams, and the longer you wait the more you'll begin to sound like everyone else.

Do any of these phrases sound familiar?
"This job is as good as things are going to get."
"I don't have the time"
"I could never make money doing what I love"
"I have too many responsibilities and it's too late now"

I grew up hearing all sorts of BS like that, too. My dad has worked in the same department since his early twenties, my mom never went to college, and growing up I was surrounded by people who simply settled for their lot in life and never tried to push themselves (though man did they ever bemoan their circumstances.) These influences led me to believe that running a business was this unattainable and foolish goal, and something not worth pursuing.

If there's anyone in your life echoing similar sentiments, tell them where to shove it. Life is too short to spend waiting around for the perfect time (which will never come) or trying to please everyone (which will never happen.) Here's a great quote on the matter:

“In every industry, there is an edge. In your business or personal life, it doesn’t matter– somewhere, there is a cliff. Most people don’t want to get to close to it, because they’re afraid they’ll fall off.

Thing is, the edge is where all the cool stuff happens. I know you don’t want to make a decision that is irrevocable and wrong– a decision from which you might never recover– that’s natural.
But guess what?

You are actually in the middle of an open field, inside your house, clutching your purse, crying like a little girl while looking at an edge you see on television.

In other words? You are nowhere near the goddamn edge.

It’s time you stopped being a fucking pussy.”
Julien Smith

Still feeling stuck? Get some help

If the idea of starting your own business is still way too daunting (and that's totally okay!) here are some great resources, articles, and people I'd recommend working with to help set you on the right track:

How to Do What You Love
An amazing article by YCombinator founder and overall genius Paul Graham

Kyla Roma
Business coach & strategist, and totally badass babe (also someone I know personally & adore)

Futurepreneur Canada
Tons of resources for mentors, coaches, funding options, etc (for Canadians)

Miracle Worker
8 week online course by Gala Darling & Ellen Fondiler

Seth Godin's Startup School
A free podcast series by Seth Godin, world-renowned marketing author, thinker and overall clever dude

Moz Learn
Learn everything there is to know about inbound marketing with this series (which I highly recommend)

Still have more questions about running your own business? Want me to expand on any of these topics? Shoot me an email, tweet at me, or let me know in the comments!