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The Truth About Side Hustling

  January 21

This post may contain affiliate links.

You know what side hustling is – all those jobs people do to make money on the side like babysitting, coaching, selling on eBay, or in my case, writing for other blogs.

I’ve noticed lately that there are a few misconceptions about side hustling or getting jobs in general. So, I’ve decided to write a post today dispelling some of those myths.

This post was inspired by a recent conversation that I had with a friend. I was trying to finish up a post that I was writing for a new client. I wanted it to be extra perfect since it was my first submission, so I was going a little Type A on it. I was running late, and when I let my friend know that I was going to be a few minutes and why, she said, “God, Cat. Don’t you think you’ve gotten enough jobs?” Now, I realize this friend might have had a twinge of annoyance or maybe even jealousy. However, I’ve also tried to help her before by sending her different ideas of jobs she could do using the amazing set of skills she already has. For whatever reason, whether it’s fear of rejection or just plain lack of motivation, she hasn’t done it. Yet, based on this remark and other conversations we have had, she somehow has this idea that I sit around sipping sweet tea and watch the money roll in.

Truth #1 The jobs will not come to you.

No one is going to wake up and say, “You know what? I think I might want to spend some of my money hiring Cat today!” I’ve been freelancing steadily for 1.5 years now, peeps, and only once has someone e-mailed me outright and asked me to write for them. And, you know what? They probably saw me write on another blog or perhaps saw something like this on twitter:

The same goes for babysitting or cutting someone’s grass. Is your neighbor going to walk over, knock on your door, and say, “Hey, could I please pay you $50 tonight to watch my kids?” No! They will not. You have to have a conversation with them letting them know you are interested in working. You have to walk over to your neighbor cutting the grass and say, “If you want someone else to do that sometime so you can enjoy the football game, I’d be glad to cut the grass for you. I only charge $x.” Sure, jobs could eventually come to you, but only when you have a recognized name, business, or referral (and you have to get up and do something first for that to happen!)

Nothing in life is handed to you. The only thing that works is persistence.

Truth #2 You will get rejected.

It’s true. You will spend a lot of time crafting a nice e-mail, updating your resume, or going to an interview, and you will be told no. I believe that this is the main reason people don’t pursue jobs or ideas. They are so afraid of being told no. I want you to look at how many times I’ve been told no just this month (and there’s still 10 days left in the month!)

Below is a spreadsheet that lists every job inquiry I’ve sent to bloggers this month. Some of these blogs advertised that they are looking for new writers. For others, I just noticed that they had contributor writers on their blogs, and so I e-mailed them writing samples and asked for a job outright. Sometimes people say they can’t hire me, but they’d like to have me guest post, which is why you see a “guest post” column in there. (I blocked out the blog names for their privacy and mine.)

To recap, this month I have e-mailed 16 bloggers to ask if I could be a paid contributor writer on their website. 7 of them have not written back. Of the 9 who did write back, 7 said no, 1 said yes, and 1 said maybe. 4 of them asked me to guest post, which I love to do and am happy to do.

I want to emphasize that that’s a good month for me. Why is it a good month? Because I got a job! Just one job, sure, but it beats doing all that work and coming up empty handed. There have been many other times where I’ve gotten all no’s, and that’s okay. Every application is a learning experience.

I use myself as an example to show you how many times I get rejected or ignored every month and yet still keep going. I understand by now that this is a part of the job. I understand that my writing might not be a good fit for every website. Whenever I am told no, I remain gracious and ask them to keep me in mind, or if they have time, let me know why they didn’t hire me so I can improve.

Nothing worthwhile comes easily.

Truth #3 You don’t have to have confidence. You just have to have no fear.

Another friend of mine recently commented on how confident I am in terms of this side hustle topic, and I nearly hit the floor. Me? Confident? Ridiculous! I’m just as terrified as the rest of you. I never send an e-mail with writing samples thinking, “Oh my gosh! They are going to love that post on credit cards!” I think, “Wow, I hope I don’t embarrass myself.”

The difference is that I have no fear when it comes to applying for my side hustle jobs. What’s the worst that can happen? 1. They’ll say no. 2. They’ll ignore me. I’ll just mark them off of that handy spreadsheet you saw above and move on to the next one. No one has ever hit reply and said, “Are you kidding? This is the worst writing I’ve ever seen!” And, they won’t do that to you either. Sure, I’ve gotten negative comments on my blog posts, but those don’t bother me. I think it’s an accomplishment for my writing to inspire enough passion in someone that they have to leave a negative remark.

Seriously, don’t be afraid. Walk up to that person and ask if they’ve ever thought of a hiring a life coach. See if your co-worker wants you to walk their dog. Take those pictures of your clothes to upload eBay even if you’re concerned they won’t sell. Just give it a try.

The only thing I am confident about is that even if I fail, I will try again.

4. You’re the only one who can force yourself to get started.

When it comes to side hustling, it’s all about you and your level of motivation. You’re the boss-lady or boss-man of your side venture. You’re not going to have someone giving you a list of things to do or people to call. You’re not going to have a superior asking you for that memo or if you’ve finished that project.

You’re the only one who can get the clients.

You’re the only one who can remain professional in spite of rejection.

You’re the only one who can make it happen.

So why don’t you?

Go ahead. Do it now.

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97 responses to “The Truth About Side Hustling

    1. Great blog Cat, as always! It does take work to get your voice out there (I know that’s how I heard about you through John). I like your “Truth #3 You don’t have to have confidence. You just have to have no fear.” Reminds me of this quote “Fake it till you become it” on this TED vid . If you haven’t seen it, I think it’s worth watching! Basically says pretend to have the confidence and it’ll lead you to opportunities (which might not have been available if you were timid) that will make you feel confident eventually. So we do gotta get our feet wet to get things going!

  1. I need to put more energy out there into finding some writing gigs. The funny part is the opposite is true for freelance video editing. I stopped putting as much energy into finding projects because 99.9% of the time it’s through recommendations or people I know. They find me.

    1. Well girlie, you had to have a fabulous reputation first to get those recommendations, so I know you were hustling!

  2. This is a really solid post. I have been wanting to get into more freelance work this year, and it’s so true that nobody is going to hand you a job. It also makes sense that if you have no fear and go up to people who you think might hire you, eventually someone WILL hire you.

    1. Thank you very much! You’re so right. Even if you’re terrified inside, you have to at least pretend you’re not scared and ask for the job!

  3. This is a great post. I am very impressed that you managed to reach out to that many people this month! Well done. The great part about getting a single freelance job in a month is it is likely to continue, giving you more and more clients.
    Your organization of your attempts to reach out is also great.

    Thanks so much for sharing, I really enjoyed reading this.

  4. I love this post, Cat! Your truths are spot on, and I love the spreadsheet you keep — might have to steal your idea and make up something like that for myself. With all the freelance writing you already do, I’m impressed that you are still seeking new gigs, and are able to balance everything. Keep up the inspiring work! Cheers to 2013!

    1. By all means, please steal that idea! It’s a great way to stay organized. Yes, I’m still seeking new gigs all the time. I just love it so much! 🙂

  5. This is an awesome post Cat. I don’t like when people think that someone is just going to give them a job. If I want extra work, I go out and look for it. It is the only way to succeed!

  6. Excellent post! That is where the word “hustle” is so important. You gotta get out and hustle whether you are selling products, selling yourself, marketing your business, or whatever, you gotta do the hustle. And you are right, fear often holds us back, but we have to remind ourselves of what is the worst that could happen? I approach them, maybe they say no. The other thing is maybe they say no now, but we never know, that situation could easily change in the near future and instead of them having to go out and seek new writers they already have your contact information.

    1. Exactly! Hustle hustle!! You’d be surprised at how many people say “not now” but then remember me later on down the road.

  7. Great motivation here to keep on hustling! I have three “side hustles” in addition to my full-time job. Friends assume I never sleep, but what they don’t understand is that a side hustle allows flexibility and you’re your own boss. And I’ll neer turn down a little extra cash. Keep up the great work, Cat!

  8. Great post, Cat! Freelance writing does scare me atm, but it’s mostly because I’m crazy overbooked already and can barely keep up with my own blog obligations (case-in-point, no new post today). But i like your hustle, you definitely do make it look easy 🙂

    1. Totally understand being busy! Plus, you have a little one and tax season coming up! Thanks for the kind words!

  9. That Excel spreadsheet is a sight to behold! If you’re that organized on the back end of things, I can only imagine how well you hold things together as you work with your clients. And what a smart idea to not take “no” for an answer by also soliciting their interest in a guest post.


  10. Awesome post. The one thing people don’t always miss is having something on their site that says that they’re looking for work. You’d be surprised at how many people click on that. I’ve hired quite a few people after they told me that have a skill set

    1. Yes! You’re so right. When I redesigned my site last summer, I added a “hire me” tab, and that helped so much. How I blogged for two years without one is beyond me!

  11. I am in the process of creating a system for bloggers to track their income from private advertisements, and the thing I’m most afraid of is rejection. The product is going to be great for bloggers (to help them save both time and money!) and I don’t need 1,000 people to sign up to make this successful, but I’m a little afraid of getting negative feedback.

    Still, I’m plugging away and when I’m ready to release, I’m going to touch base with every blogger I’ve done a favor for over the past few years. Hopefully I’ve built up some goodwill!

    1. You should absolutely go for it, Daniel! It sounds really interesting, and for the record, I think goodwill and karma go a long way!

      1. Sicorra at tackling our debt has a pretty neat blog organizer that is free to download. Great post! If you don’t do anything you won’t go anywhere.

        1. Hey Pauline! Thanks! I know; I love Sicorra’s blog organizer! I’m going to do a similar post soon that was inspired by her. 🙂

  12. This was a really good post and applicable to any walk of life where it concerns going after what you want. I know that these tips helped me in part to be where I am today in my life and career. So many say “Oh you’re so lucky blah blah blah”. Luck has little to do with it! Congrats on landing the job you did and being tenacious with your output 🙂

    1. Thank you so much K.K.! Good to know these tips worked for you as well. It’s nice to know that down the road, hard work keeps giving rewards!

  13. “Nothing worthwhile comes easily.” Amen and Amen Cat!! Awesome post. That phrase is one of my favorite sayings to live life by. Sure, something might just drop in your lap…but that is highly unlikely. Anything worthwhile takes time and effort. I know it’s not easy, but it’s what gets you ahead in life and in this case able to bring on more side work.

    1. Thanks so much. I completely agree with you, and it’s good to know there are others with the same philosophy!

  14. Love the attitude Cat! Didn’t realize you did so much freelance writing! Gotta love being able to do so from the Caribbean or anywhere in the world. Good stuff being so organized.

    I’ve been rejected so many times or ignored it’s comical. But, each rejection fuels me to do more. You can just channel all the lost opportunity with writing on your site!

    Go Tribe!



    1. Thanks very much! For sure, you have to get a bunch of “no’s” before you finally get that YES!

  15. Super informative post. Everything about our world has become so instantly easy that I honestly think people forget how to work for what they want! Good job 🙂

  16. Great Post Cat!
    It’s true even with blogging we have to just get out there and network as the fans aren’t always going to just drop into our blog on their own we have to show them what we’ve got and invite them in. In your case even a simple guest post might entice a blogger to pay you next time around because what you wrote generated alot of interest on their site. It’s worth the time to say, sure I’ll do it. There’s plenty of successful people out there in all facets of life that did things free at one point or another in their career that got them to where they are. It’s not always about the money it’s about showing them what you’ve got and if they want it, or want more of it then talk business. I like how you put this on the table. Great job. Mr.CBB

    1. Yes, this definitely applies to blogging in general! Thanks, Mr. CBB! One of my goals this year is to guest post more. I’ve done a lot of work for free, and that’s definitely a great point. I actually learned how to use wordpress during an internship that I did for free. 🙂

  17. This is a great post Cat! I’ve been freelancing for about the same amount of time (Since FinCon ’11) but haven’t been nearly as good about seeking out jobs. Therefore my job list is much smaller. I’d like to add more to it but haven’t really taken the right steps. Mainly because I want to switch out of the PF niche and write more in what I know which means making New contacts. This post is a great reminder of how I need to go about doing it.


    1. Hey Jessica! Glad to help. I actually switched into PF, so I definitely understand building new contacts, etc. I wish you the best of luck! You can definitely do it!

  18. These are all really good points. Especially No 3. I’ve never considered myself to be very confident, all knowing, or even qualified to do certain things. But I do have something in me that says “if I don’t at least try, I’ll never know …” Most people would be surprised at how different their lives would be if they just went for it!

    1. I love your last sentence. Although I “go for it” quite often, sometimes I do hold back, so it’s great to have a reminder!

  19. I actually just got my first real freelance gig for a financial site. I’ve been applying here and there but my rates have been pretty steep since I don’t really need the extra money. Doing it more for fun and to build up a small portfolio to showcase to potential employers should I ever need it.

  20. I really like the point about not having to be confident, just fearless. Fear of rejection is normal and I think it holds a lot of people back. I appreciate your fearlessness in showing how many people you outreached for writing gigs :-). A lot of the jobs I’ve gotten in the past (waitress and nanny) I’ve gotten by just been putting myself out there and asking if people needed help. I think asking for jobs is a little bit of a lost art. We “apply” but we don’t really “ask”.

    1. I like how you say asking for jobs is a lost art. I definitely agree, and I think it makes those who do ask stand out more.

  21. I’m on my feet APPLAUDING!!! People don’t always understand your hustle and the fact that you have to keep the gigs rolling in for the very slow times… you can’t stop. I’m definitely sharing with my clients and friends who are always saying they want to ‘do their own thing’. Doing your own ‘thing’ is often harder than your 9-5, so you have to be ready for it. Love it!!

  22. So true! I know so many people who say how lucky I am to have various means of income/side hustles. What they don’t see or believe most of the time is exactly what you said – you have to put yourself out there, you do get rejected, you have to find the jobs etc. I was fortunate that a few of mine came to me (such as a publishing contract and my first few writing gigs), but for the most part, if you don’t put yourself out there and look for the jobs, without fear, you will get nowhere!

  23. Pingback: Carnival of Retirement - Super Bowl Week Edition | WorkSaveLive
  24. Well put! I have a spreadsheet similar to yours with guest posting leads and such. I use that to to write reminders of additional requirements those blogs are looking for if I do get rejected and they are gracious enough to give me feedback. An example I can think off the top of my head is this blogger really liked my post, but didn’t mention he wanted longer posts (at least 1000 words) until I finished a draft for him.

    I think I might have to make a spreadsheet like yours with paid gigs. I have a system right now going in my head, but I have a feeling my brain will be too full one of these days lol!

  25. I just found your blog and have been shamelessly devouring your archives all morning! So many great posts. I especially appreciated the spreadsheet you shared here. I’m starting to look into guest posting as a way to grow my blog and online presence, and going about it with no system for staying organized would be super stressful. I’m working on a spreadsheet based on yours to help me stay on track. Thanks so much!

    1. Hi Alicia! I know I sent you a “hi!” e-mail but I just wanted to respond to your comment on here too. I’m glad you liked the spread sheet! Good luck with your side income!

  26. I completely agree with every point you have made. I have been working on getting freelance writing assignments over the past few months and my experience is very similar to yours. I constantly email blog owners and apply to job boards if they have relevant openings. A lot of the time I don’t even get a response back. I would say that I probably get one job for every 25 blogs that I query, if I’m lucky! Getting jobs is the hardest part.

  27. Very lovely blog! And this particular post is encouraging and motivational. Keep up the good work! Thanks for sharing!

  28. Thanks for putting it in perspective.
    I am currently in the process of applying to jobs, and I find myself not even thinking about applying to certain positions out of fear of rejection.
    I know that I should find a way to overcome this fear, and that doing so will put me in a better position, but I am still trying to make that leap! Thanks for another great post.

  29. I worked in telemarketing for 2 years and part of the job was being rejected every 5 minutes. I’m more used to being told no than a lot of people are. I still have fear and I just go for it anyway.

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