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Looking to Launch a Side Hustle? Here’s What You’re Really In For

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It’s a dream many of us have: launching a side business in our spare time that will one day grow so big we can officially quit our 9-5.

I’ve been living the day job/side hustle double life for six months now, and I’ve come to realize it’s not quite the glamorous vision I had when I first started (which largely involved me banging away at the keyboard at 2 a.m. while “She Works Hard for the Money” played inspiringly in the background).

If you’re genuinely interested in joining the league of side hustlers, I’d like let you know you’re getting into:

Work is still work. I adore writing, editing and anything related thereto — so freelance writing and editing truly is my “dream job.” But work — even work you love — is still hard, and just because you enjoy doing it doesn’t mean it won’t be exhausting at times. Especially if you’re trying to squeeze it into the evenings and weekends around a full-time job.

Be prepared for some resentment and frustration. Be prepared to get tired of the thing you love sometimes. It doesn’t mean you’re on the wrong path or that you don’t still love it. It just means it’s work. And work isn’t always fun.

Get used to 24/7. You know to expect some late nights and early mornings when you’re trying to pull off a side hustle in addition to a regular job. But you’d better get used to juggling this new, always-on schedule, because even if you manage to make your side hustle a full-time gig, the hours probably won’t change all that much. It might be a little less stressful because you won’t be torn between two sets of schedules, but a work-for-yourself life often requires you be available far more than at a traditional 9-5.

You will suddenly find a million previously dull things infinitely interesting. When you finally make the commitment to attack your side hustle for real, you will suddenly find yourself deeply compelled to attend to all sorts of random things instead o f your side hustle. This is the result of several factors: fear at failing if you begin, passive-aggressive resentment of all the work ahead of you, procrastinating because you’re not sure where to start.

A priorities list is your best friend as a side hustler. Not a To Do list (which just lets you pile up tons of things you’ll feel guilty about never getting around to), but a simple, actionable list of the 2-3 big things you need to accomplish that day. Get those done first, then worry about the rest if you have time. No matter how psyched you suddenly are to tackle that loose tile in the basement you’ve been ignoring for 10 years.

You will wonder why you’re doing it. Wouldn’t it just be easier to go back to the way things were? Were they really so bad? At least then I had some down time…

These are some of the things you will find yourself thinking, secretly in the back of your mind, even though you feel guilty about it. Because hustling is hard. It takes a lot of persistence, prioritizing, and sheer moxy to pull off. It’s only natural that at some point you’ll find yourself longing for the days when you could leave work behind once 5 p.m. hit, go home, and zone out in front of Dancing with the Stars with no other care in the world.

My strategy when this false nostalgia hits? Reminding myself why I started my hustle in the first place: Because I was miserable with the way things were before.

Other people will second-guess you. You’ve already got a job. You deserve a little rest. Be honest — are you ever really going to get this business off the ground?

These are some of the things your well-meaning friends and family will say to you when they find out what you’re trying to do. If they say them around the same time you’re saying similar things to yourself, it will be especially tough.

But hold to your dreams. You embarked on this crazy quest for a reason; keep reminding yourself of what that is, and don’t let the well-meaning naysayers discourage you.

You’ll get a glimpse of what you’re in for (and whether you’re cut out for it). Most people launch a side hustle in the hopes of one day working for themselves (cue to images of sipping mimosas on a beach with a laptop on your sun-warmed legs).

But the truth is that working for yourself isn’t necessarily easy; it’s just a different kind of challenge than being “in the grind.” It requires a whole different skill set of dedication, discipline and hard work. Which is why a side hustle is a great trial period for anyone thinking of working for themselves.

It gives you a chance to see what you’re getting yourself in for and to decide whether it’s right for you before you cut all ties with your steady paycheck. It gives you a chance to learn important self-employment skills like how to juggle multiple priorities, manage your energy and develop a work-life balance that works for you.

Mastering a side hustle may be a challenge, but if you dream of something better, it’s a great way to test the waters.

Kelly Gurnett, a.k.a. “Cordelia,” runs the blog Cordelia Calls It Quits, where she documents her attempts to rid her life of the things that don’t matter and focus more on the things that do. You can follow her on Twitter and Facebook.

Brazen powers real-time, online events for leading organizations around the world. Our lifestyle and career blog, Brazen Life, offers fun and edgy ideas for ambitious professionals navigating the changing world of work.

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  • http://www.abbyhasissues.com/ Abby

    So true. But I’ll be honest and say that although I “side hustle” for a publication within my company with contract work, I don’t do any work on the side away from that simply because I work my tail off at my job for that steady paycheck (and additional side gig.) I’m not sure I have enough passion for the technical part of what I do–editing and writing away from the blog–to not go insane, as I really have no idea where I would start. Plus, when I did freelance away from my company, the pay never ever equaled the effort. And without the passion to drive that effort, the money did become a factor.

    That said, the time I could spend “hustling” is spent on my blog, something I DO have a passion for but that I’ve never made a penny off of. While I would love to marry the effort, the passion and the profit, I’m realistic right now that sometimes I do have to do what I don’t want to do so I can do what I want to do with the time that is my own.

    Now I’m rambling, but I’ve been on both sides of things. Freelancing is great if you’re adequately compensated for your time and effort–which I’m sure you are–but for me, I’ve yet to find a niche that satisfies my need to create with my need to pay the bills. So I do the daily grind and look for a bit of release with the blog (although I stress myself out with that too.) That doesn’t mean I’m not always looking for new opportunities, but I have to have passion for anything extra. It’s not all rainbows and unicorns. Great post ;)

    • http://www.cordeliacallsitquits.com Cordelia

      It’s so true–it can be incredibly frustrating to slave away at your day job and then come home to even more work, even if that work is something you enjoy. You definitely need to monitor what you’re getting out of side hustling vs. what you’re putting in.

      Maybe you’re not making a ton of money hustling, but you abso-freain’-lutely love whatever is it that you’re doing, so that passion (excellent word) is enough to fuel you to keep going. Or maybe, like you’ve found, there’s a way you can pursue the thing you enjoy as more of a hobby and be happy with that. It’s definitely not something for everyone. (Or all rainbows and unicorns.) :P

  • http://twitter.com/amandaabella Amanda Abella

    This is great Kelly! I personally think a side hustle is a great way to test the waters (although I did it totally backwards lol). Either way its always nice to have an extra source of income and I’m glad you tackled all the challenges that come with it :)

    • http://www.cordeliacallsitquits.com Cordelia

      It sounds like you definitely jumped in feet first, but I’m so impressed by how far you’ve managed to come so quickly. You definitely learn by trial when it comes to side hustling–it’s an experience like no other.

  • http://www.writeabio.com/ Barbra @ Write a Bio

    This is great advice. I come from an entrepreneurial family, and have been self-employed most of my life, so these points seem self-evident to me. But this article brings up some really important issues for folks for whom these points are not self-evident.

    • http://www.cordeliacallsitquits.com Cordelia

      You’re very lucky to have grown up in an entrepreneurial family. One of the difficulties faced by a side hustler is reactions from friends and family who can’t understand why on earth you’d want to try something so challenging and uncertain–especially when you have a “perfectly good” 9-5. It’s an entirely different mindset, and the reality of the day to day hustle can be quite a surprise for someone who’s never really seen how it works.

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  • http://kontrary.com Rebecca Thorman

    I really enjoyed this post. Most people don’t write about the truth of having a side job, or pursuing your dreams. It is SO tough. I think it’s because you have to break a whole bunch of existing habits and start new ones. And then there’s all this extra pressure you put on yourself. Oy.

    • http://www.cordeliacallsitquits.com Cordelia

      Oy indeed!

      It’s definitely not an easy path to follow, but if brings you purpose and fulfillment, then it’s 100% worth it. And hopefully, one day in the not-to-near-future, it won’t be a “side” hustle anymore, but your full-time hustle. :)

  • http://techbizgurl.com Jessica Williams

    This is such a great and timely post considering I have definitely had issues wondering why I’m doing my side hustle instead of relaxing at the end of a long day. But I keep going with it because it’s different and because of it, I’m meeting so many new people and growing my network. That would not have happened otherwise. So that’s one of the things that keeps me going.

    • http://www.cordeliacallsitquits.com Cordelia

      I so feel you. I have plenty of moments where I wonder if I wasn’t stupid for not just staying in my 9-5, writing a little in my free time, and basically having less pressure. But for all the stress and hassle that my side hustle gives me sometimes, I’m still overall much happier pursuing this than I was when I was doing the 9-5 alone and was bored and frustrated. It’s hard work, but for me, it’s completely worth it.

      • http://twitter.com/DerekTac Derek Tacconelli

        Cordelia, I am there with you 100%!!! One reason I chose to undertake my side-hustle was because it filled a creative void. It is extremely frustrating having creative work on your mind while stuck in the office. I guess we know why the caged bird sings.

        One tip I have here for this is: Concentrate in the NOW. There will be time (but maybe not energy) later to tackle concepts for later. I like to use my brainless-task time to brainstorm ideas, and just jot a quick note down for later

        • http://www.cordeliacallsitquits.com Cordelia

          I agree: Concentrating on what you can do, right here and now, to advance your projects is the best you can do (and, honestly, all any of us can do). When you’re doing the day job/side hustle dance, it’s so easy to feel overwhelmed and pressured into needing to do a million things at once to keep up with everything. But all you can do is chip away at your projects, focusing on giving whatever you’re doing right now your best attention and effort. Just knowing that you’re working on something, and making progress, can help to get through those soul-dulling hours at the office when you’re stuck wishing you could do your “real” work.

  • http://how-to-improve-english.net/ How to Improve English

    good post you have here… Most people don’t realize how much time and energy a side gig takes. And most of the get-rich-quick junk obviously doesn’t want to describe a barrier on obtaining a side income… Thanks for the hard work!

    • http://www.cordeliacallsitquits.com Cordelia

      You’re right; there are a lot of “earn hundreds now!” programs that guarantee you can make millions working from your home. But the truth is that “get rich quick” isn’t how it works; it’s more like “get rich from good, hard, old-fashioned hustle.” Working for yourself isn’t any less work than working for an employer; it’s just a different variety and lifestyle.

    • Taniakarpowich

      i’m absolutely agree with you! i like your point of view! http://ti-albums.net/

  • http://edwardantrobus.co.cc/ Edward – Entry Level Dilemma

    There are all kinds of side hustles. Many of them are as you describe, but not all. I just started a side hustle where I drive designated drivers from a service back to the down-town area where all the bars are. 2-3 hours a night, 2 nights a week. I’m making about $25 a night, and I spend half the time sitting in my car reading a book.

    • http://www.cordeliacallsitquits.com Cordelia

      It’s true, there are all sorts of side hustles. I’m impressed with your creativity in coming up with yours–that sounds like a service that could help many people.

      • http://edwardantrobus.co.cc/ Edward – Entry Level Dilemma

        Alas, I can’t really claim the credit for that. My housemate started the service and when it started to grow to the point where he needed more drivers, he asked me to join.

  • http://twitter.com/DerekTac Derek Tacconelli

    I love this article! You hit upon many topics I have been discussing with myself and my peers over the last 7 months. I have my steady 9-5, it gets the bills paid and helps give me more monetary ‘freedoms’.

    Right now I’m using my “side hustle” as a means to pay off my student loans. I am a freelance video editor, getting projects about once a month (they usually take about 2-3 weeks total to complete). I constantly have to remind myself, that:

    A) My side hustle is great for the advancement of my career and time-management skills
    B) Remember my goal of paying off my loans in 2 years
    C) To fulfill my creative needs/wants. I am a creator, my parents are creators, I must CREATE!

    Your article is a great example of how minor tasks can seriously hinder progress on your side-hustle. I struggle with this daily!

    • http://www.cordeliacallsitquits.com Cordelia

      It’s definitely not an easy thing to do, and there are so many distractions/hindrances that crop up in spite of the fact that you really do love your side hustle and want to give it your all. I think being aware of these pitfalls, and realizing that they’re normal and don’t mean you don’t care enough about your hustle, is a huge step towards getting past them.

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  • http://www.jaywiese.com Jay Wiese

    Someday/maybe list

    Better to capture those unimportant items on a “someday/maybe” list just to get them out of your head. On the off chance you find yourself with some idle time, you can knock something off this list.

    • http://www.cordeliacallsitquits.com Cordelia

      A very good idea. I have a similar list–instead of a set “To Do” list of things I have to get done each day, I have a “rolling” To Do list. I write down whatever the next steps are in the projects I’m working on (a new chapter in my ebook, reaching out to someone for a guest post, etc.), and when I have a few spare minutes, I cross that item off and add the next step to the bottom of the list. It makes sure I keep basically on top of things and nothing falls through the cracks, but it’s a lot less stressful and pressure-filled.

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  • http://www.ehustleonline.com/ How-to-work-at-home

    Wonderful post! Although working for yourself has its challenges, it’ll definitely pay off in the long run with hard work and persistence.

    • http://www.cordeliacallsitquits.com Cordelia

      Agreed! I’m hustling my tail off right now, but I know that it will ultimately be so worth it.

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