On Monday, I shared the lessons I’ve learned from my 2 ½ year journey to launch a side hustle, grow it, and ultimately leave my day job for good. You’ll need to know these before we move on to the logistics of this kind of Quit, because if you ain’t got the right moxie for this, no how-to guide will be able to help you.
If, however, you’ve reviewed and assimilated said moxie, then today I would like to share with you the overall strategies and tips that can get to you where I’ve gotten me (i.e. living the life I always wanted to live, on my own terms, through my own design).
So, take out your notepads (does anyone actually use those anymore? English nerds—any Moleskin fans out there?) and get ready. ’Cause here they come…
Don’t Quit Your Day Job (Just Yet)
I know this is probably the last thing you want to hear once you’ve decided to make a go of the Ultimate Quit, but at least for now, keep that steady, well-paying (or at least paying) job.
Starting your dream off as a “side hustle” while still working your day job has a number of practical benefits. It gives you the security to keep the bills paid as you grow your side business, which in turn allows you much more freedom to: a) make mistakes, b) try different things, and b) turn down offers that don’t seem good enough for your dream. These are all critical things to be able to do when growing a successful business.
If I’d relied solely on my freelance income from the get-go, I would have gone down in flames, and fast. I would have found myself taking on all sorts of crappy projects just for the sake of a paycheck rather than tweaking and honing my services until I had a portfolio of projects I truly enjoyed. And even with taking on every crappy gig I could find, I still would have had serious trouble paying the bills—especially considering how unforgivingly Uncle Sam taxes freelancers. I’m estimating I probably would’ve made it for 2-3 desperate, anxiety-riddled months before I gave up on my dreams and crawled back to the 9 to 5.
So don’t view your day job as your mortal enemy, as least not at first. It can actually help you achieve your dreams if you view it right—and really, what’s sweeter revenge than knowing your day job ultimately helped you quit your day job?
Hustle Like Hell…But Also Take Care of Yourself
Working a day job while starting a side business is not easy. If it were, more people would be striking out on their own every day. This is a trial by fire period where you’re going to be tested to the max—but it’s also a chance to gain some priceless skills like time management, dedication, persistence, and perspective.
When you’re finally on your own, there won’t be a schedule to keep you on task or a boss to peer over your shoulder. This is freakin’ awesome, of course, but also puts a lot of pressure on you, because now you’re the one who has to regulate yourself.
So use this period of extreme busy-ness to figure out how you work best. Are you super-energetic in the morning but draggy in the afternoons? Then get up early to work on “your” stuff before the workday starts. Do you have to ply your eyes with caffeine to stay open long enough to finish a project after a long day of work? Remember these nights—the nights when you could very easily have given up, but kept pushing because it meant Too Damn Much to you—and hone that persistence to a precise weapon. You’ll need it later when it’s time to promote your services, negotiate with clients, and otherwise run a biz single-handedly.
At the same time, don’t forget to keep yourself from, you know, falling apart at the seams. There’s a culture among hustlers that holds up exhaustion, long hours, and relentless work as the paragon of a true hustler. But the truth is, for most of us average humans, you need to allow yourself a chance to step back, breathe, and recoup from the (double) grind from time to time. Keeping yourself in one piece is the only way to keep your business moving. So don’t neglect the “you” time, k?
Step Down Strategically
I transitioned myself from day job to dream job in several carefully planned and executed steps. First it was Freelance Fridays off, then it was down to a part-time schedule at the day job, then it was finally time for the Quit of Quits.
At each of these steps, I made sure I knew exactly what I was getting into. I ran the numbers, checked my budget, and made sure I was relatively comfortable that, although the transition might be a little rough initially, I wasn’t going to put us out on the streets by doing it. I knew I had enough leeway to make each leap, which made each leap much safer (and more successful).
I was fortunate enough to have a very understanding boss who valued my work and was willing to be flexible about my arrangements. You may need to step down by quitting your full-time job to go to a part-time one instead. But whatever you do, don’t make the next leap until you’re reasonably sure you can afford it. A little wiggle room is o.k.—you’ll likely make up that difference in no time once you’ve got more time to devote to your biz—but make sure you can still cover the big things like food and housing, especially if you’re not the only one along for this crazy ride.
Get Things in Writing
I’ll admit that some of my smaller projects are on an as-needed basis, but I’ve worked with these clients long enough to know that their business is steady and they respect me as a freelancer. I’m willing to accept the risk that, should they no longer need my services, I’ll have to find a new project to fill that gap in my income.
But for clients you haven’t worked with in the past—or for projects that would represent a large portion of your income—get everything in writing: the terms of the project, the scope of the work, deadlines, payment amounts, how long you’ll be working together. This is your livelihood you’re talking about, and you have every right to make sure you secure it as much as possible.
I learned that the hard way myself, and I won’t make that mistake again. When I got the new offer that allowed me to Quit at last, I made absolutely sure a contract was agreed upon and executed before I turned in my notice to the day job. Even though it was a client I’d worked with for years, it was a big project and a big leap I was about to take because of it, and I wasn’t about to play fast and loose.
Remember: your dream business is still a business. Always treat it as such.
Are you currently living the day job/dream job double life? Then you’re in luck, because I’m currently working on a guide to help people in just that circumstance! You can help me make it as crazy-useful as possible by filling out this quick survey telling me exactly what you’d like to see.
Not to say I will spend more at stores that are overpriced and give me food and wine to make me feel good, but I refuse to go to stores that sell small sizes that I would have worn as an under-weight and inappropriate teenager.
I only shop at these stores because they are inexpensive and I can find pieces like blazers and skinny jeans, which are hard to for me to afford anywhere else. For some messed-up reason, I feel that is the definition of frugal.
I Feel Fat
In spite of any savings I might get, these places make me feel fat when I wear the Large or Extra-Large that they never have in stock. Just seeing styles stocked in only sizes 2, 4, 6, or even 8 makes me feel fat.
I cannot fit into an 8 or 10. Maybe a 12 if it’s stretchy, but nothing is stretchy—not the way it needs to be. I know I’m not fat, but only those stores can make those emotions come out. I don’t know why my frugal mind does not get that my emotional mind is more important and I can go without some clothes.
I Am Actually Very Much in Shape
For my age and height, I’m a decent weight, and pretty fit as I ride my bike often to deal with daily stress in life. I run occasionally and might start more if only to fulfill a New Year’s goal. (I hate running.) I love dance video games and getting outdoors, and I can run through Denver International Airport with 15 minutes to get from the ticket counter to the airplane before it closes early (with bags).
I have to say I am in shape and feel good, so I need to stop letting these stores control my feelings.
Every time I go into one of these stores looking for a deal in search of something I could wear for work or fun, but I always end up feeling unhappy. But stores cannot control my feelings. No one can; only I can control my thoughts and feelings. I’ll quit fashion all together if it makes me feel bad about myself in any way—I quit their e-mails and Facebook posts, their coupons and advertisements, I quit trying to squeeze into something someone else thinks is cute. I quit cute.
I Choose to Be Me
So, I choose to spend my money elsewhere. In stores that do not make me feel bad—in stores that get I am frugal, but that I also love to look good. There are so many stores out there; I can select as I please. I do not have to pick the inexpensive ones that just came to town. I can pick whichever ones I want.
I know I am a strong, lovely, logical, intelligent person. No one can control that, so why should I let something like clothes have control over me? Instead, I choose to be happy, healthy, and beautiful while being the best “me” I can be.
LB is currently a 4.0 student working towards a dual bachelor’s and master’s degree in business management. She writes about her struggles using a $50,000 income to pay for school, give back to the community and find time to live life while staying out of debt. Check out more at The Financial Black Sheep.
Interested in submitting a Reader Quit of your own? Check out how here.
I’ve learned a lot over the course of this ridiculous, beautiful, frustrating, exhilarating process called Chasing My Dream. And, as promised on last week’s Quit of Quits post, I would like to share those things with you.
Wednesday’s upcoming post will focus more on the practical, how-to steps that can get you to your own Ultimate Quit. This post is instead about something that, I think, is even more important than how-tos: the take-no-prisoners, hell-or-high-water attitude you need if you’re ever going to make something like this happen.
Because the percentage of people who try to chase their dreams and then give up is a damn shame. Every day, people jump on the Follow Your Dreams bandwagon—and every day, plenty more jump off like the wagon’s on fire.
I don’t want your wagon to be on fire. I want it to be a chariot that flames only in the sense of “Holy crap, that brilliance is blinding me like the sun!” And, although the strategic how-to bits are an important part of achieving that brilliance, they’re only the framework. If you don’t have the right attitude, all the how-tos in the world won’t take you very far.
So, after 2 ½ years of trial by fire (apparently I’m all pyro in this post), here are the most important things I’ve learned about making your dreams come true:
1. Believe you are freaking amazing—and then act like it.
When I started this blog in November 2010, the only readers I had were my mom, my husband, and my best friend from high school. But I decided that if I was going to do this thing at all, I was going to write every single post like I was Ash-frickin-Ambirge with a million rabid followers.
I addressed my 3 readers as if they were the massive posse I someday hoped to assemble. I spoke as if I’d already established myself as someone worth listening to. I exuded all the confidence and snark and brazenness I hoped would one day be validated by actual results. And when people stumbled onto my site, they liked it, because I sounded like I was way more pro than I really was. I didn’t sound like someone who was trying this on a whim and a prayer because she’d been inspired by watching Julie & Julia (dirty little CCIQ inception secret).
My first few months were a learning period. My writing was rusty, my style was a little stuffy, and the more comfortable I got in the Cordelia persona, the better the posts became. But the important thing was that, even though my skills needed some work, I came out swinging. I made it sound like I was someone worth listening to, and, to my great astonishment, people listened.
2. Never, ever, ever think it’s too late. (You hear me?)
If you haven’t read my post on what my life was like before CCIQ, take a look at it here, and then come back to keep reading. Because if anyone was ever in a place to believe their dreams had crashed and burned to an unsalvageable heap, I was one of those people. And yet, here I am.
If you have the drive within yourself to do anything—start your own business, pursue your painting, move abroad, raise miniature alpacas—and that drive keeps pestering you in the lonely hours of the night or when you’re idling at a stop light, listen to it. Then go the fuck after it.
We are all born with a talent. I don’t care what it is, how “marketable” it seems, or how humble you are about it; your one and only purpose in this life is to pursue that talent like a psychopathic stalker. Because if you don’t, the world will be the sadder for it, and you will know, every day of your life, that things are not as they could be.
Take a chance. Give it a try. Don’t look at statistics or likelihoods or projections or past results. Just go. Then keep going.
3. Put yourself out there. You’ll be amazed how often it works.
When I first put up my Hire Me page, it was on a whim and a particularly bad day when I was hating the day job with a passion and figured what did I have to lose? Turns out that was the same day my new friend J. Money gave me a shout-out over on his blog. One woman in particular saw his post, visited my site—where she happened upon my (ta-da!) brand-new Hire Me page announcement—and became my first-ever freelance client. That same woman is the client who just gave me the extra income I needed to Quit at last.
I am a firm, die-hard believer in the notion that if you open yourself up to the possibilities that are out there, take chances, and believe they could work, the universe will deliver. Not in the woo-woo, “put a bicycle on your dream board and one will show up on your doorstep” way as promised in The Secret, but in the legit fact that being available and ready (and declaring you’re available and ready) will put you in a better position for opportunities to come your way—and a better position to seize the hell out of those opportunities when they come.
4. Make friends in high, low, and in-between places.
One of the first things I tell people who ask me for freelance advice is that 90-95% of my regular work comes from referrals and word of mouth. In fact, a good 80% of that comes from referrals from one contact in particular. None of this was done strategically—I just made friends, did my best work, and the referrals started coming in of their own volition.
Network with everyone—A-listers you think would never give you the time of day, people at the level you’re currently at, up-and-comers you can tell will one day be A-listers themselves. You never know where an opportunity will come from. Forging and nurturing genuine relationships with the people you admire and relate to will increase the number of doors that could open to you exponentially.
And note that word “genuine.” Cutting and pasting form e-mails to strangers or randomly blasting your latest product to everyone on your contact list is amateur hour (and totally worthless). Be real, be awesome, and the “networking” will take care of itself.
5. Momentum accelerates, and hustle is unstoppable.
I’ve said it before, and I’ll say it again:
Hustle + passion + a dogged refusal to give up can take you places.
There is no special skill, no magic formula, no guru how-to guide that will ever take you farther than the sheer, bullheaded determination to make things work, and the follow-through to do whatever it takes for that to happen. If you’ve got that, you will make progress. You can’t help but make progress.
If you take a look at the timeline in last week’s post, you’ll notice that each step in my Quits journey came faster and faster the farther I went along. It took me a year after starting CCIQ to go down to Freelance Fridays, then another year to go down to part-time. Then it was 6 months till I was ready to Quit altogether. And—after the extreme blow of losing an entire half of our income—it was one month to the day before we’d regained our footing enough for me to forge on with the Quit.
Hustle builds upon hustle. It’s slow going at first, but the more you put in, the more you get out. Don’t give up because things aren’t moving as fast as you’d like them to or because you encounter a few roadblocks. As you keep chugging along, the momentum will be building behind you, until one day it picks up enough force that you find yourself shooting forward without quite knowing how it happened.
Keep hustling. Keep pushing. Keep believing. Take the hits on the chin and get back up as many times as you need to.
It’s what separates the wagon-jumpers from those who make it to the end. Just take a look at that sorry guy in the picture above. You don’t want to be that guy. You want to be the girl who’s kicked his ass.
And there’s absolutely no reason why you can’t be.
[Part of my mission to “live deliberately” involves ruthlessly cutting out anything that saps my time, energy or money to no good end. I’m calling these things my “Quits,” and this is one of the many items that have found themselves on my Quits List.]
Sit down. Take a breath. Grab a glass of water (or bourbon).
There. Now that I’ve done that, it’s time to announce…
Today, I am giving my notice to the day job.
I am finally Doing This Thing.
No, I don’t quite comprehend it, either. But there it is. The ultimate Quit of Quits is happening.
Holy mother-effing Moses.
The (Slightly) Long(er than Expected) and Winding Road
Just like every other step on this crazy journey to freedom, this recent development went down in a surreal manner that felt both much quicker than I anticipated and way too freakin’ overdue.
One month ago to this day, I had my resignation letter written and ready to hand in. I’d been hustling my little tail off, and things had reached a wall. No one but my husband (and occasionally my mom, who was at the end of a few sobbing phone calls) knew just how bad things had gotten in my head, but I’d reached the breakdown point. So it was time to leap, come hell or high water.
I wasn’t 100% sure how I was going to finance it, but I was about 75% sure, and the other 25% consisted of sheer determination and a desperate desire to make things work.
Then life hit, and everything went on hold. But I reminded myself (daily) that things would work out, because somehow or another, they always had.
A little more than 6 months before I wrote that first, ill-fated resignation letter, I’d gone down to part-time at the day job after realizing I’d hit another wall (and breakdown point) and there was nowhere to go but forward. I wasn’t 100% sure how I was going to finance that leap, either, but again, I was about 75%, with the other 25% consisting of the aforementioned determination and desperate desire.
A little less than a year before that, I’d taken off Freelance Fridays, that time relying on more like 90% certainty and 10% willpower. But still, it was the first step towards making my ludicrous dreams a reality, and it was a big one at the time, one that felt just as risky as the others.
Throughout all of it, I kept moving forward, and with each leap, the universe caught me. Call that hippy-dippy-trippy if you like, but the universe and I have gotten on very intimate terms through all this, and I respect the hell out of that glorious bitch. If you demonstrate you’ve got the moxie to make things happen, she will give you those things to make happen. She’s got your back—if you prove you’ve got the hustle.
So when the shit hit the fan a month ago, I had enough of a track record with said universe to believe that the road would straighten back out eventually.
I just had no idea it would straighten out in less than a month. But, that’s the universe for you.
Here’s how it went down:
The Final Step
I was emailing with (my new favorite) freelance client on Monday about a current project we’re working on, and I happened to mention that I was on the verge of Quitting at last and looking for a few extra things to make that possible.
I wasn’t any more on the verge of Quitting than I’d been since we lost half our income; I was just frustrated as all hell that particular morning and desperately trying to drum up more business to keep myself from jumping out a window. I’d already sent out several emails and status updates attempting to fish some more opportunities out of the universe, and although I’m always optimistic, I wasn’t prepared for anything to come of it.
But my client wrote back within minutes and said she’d been thinking about giving me more projects; what could we do to make this happen? After an afternoon of email negotiations, we had a contract in place for a monthly flat fee that was just enough to make my Quit possible again. There will still be a gap in the finances, but this gives me the basic security I need to leap, knowing I have several other things in the application stages and it’s just a matter of waiting for a couple to come through.
I have every faith that they will.
So that evening, I revamped my resignation letter, and this morning, I’m handing it in—one month to the day after I thought everything had been shot temporarily to hell.
The Speechy Bit (stay tuned)
At the risk of losing you with a waaaay-to-long post, I’ll save my “here’s what I learned from all this craziness” speech for Monday’s post.
But suffice is to say, hustle + passion + a dogged refusal to give up can take you places. I’ve been seeing that firsthand throughout this whole journey, and it’s finally taken me to the end game I envisioned two and a half years ago.
I am finally Doing This Thing.
Holy mother-effing Moses.