May 2014

4 Simple Keys to Side Hustle Success

side hustle success image

Welcome back to another edition of the Side Hustle Shuffle. My previous two posts, on getting started and finding paying clients when you’re new to the game, focused on some actionable tips anyone could apply to their own efforts in establishing and growing a side hustle. Today, I’m going to concentrate on offering more in the way of advice that you may not be able to immediately act on in a tangible way – but I hope you still find it helpful and meaningful in a way that allows you to take these words to heart.

If you’ve never run five feet in your life, running a 5k might as well be impossible. At least, that’s how we perceive the challenge in our minds.

When you’ve never done something – or if you have tried it but failed once or twice in the past – it can seem like it simply cannot be done. Never mind the people that are out there doing it. They must have known some secret, had some advantage, or are enjoying circumstances that are simply beyond your own.

Maybe successful people had connections. Maybe they had money to get them where they are.

Or maybe they just got fed up of negative, self-defeating thinking. Maybe one day they woke up and said, I am just going to start and simply starting would be the goal.

That’s the secret, right there. Just start. Imagine how far along you’d be right this very moment had you just started a year ago. Or two years ago.

Feeling like that doesn’t apply to you because you’ve failed in the past? Failure isn’t bad and it doesn’t mean you’ll never succeed. Our failures can drag us down, but only if we let them. So flip your mindset around. Understand that your failures are merely stepping stones to a future success.

If you’re open to evaluating and analyzing the experience, every time you give something a try you’re opening yourself up to a learning opportunity. Take advantage! And don’t fear failing. The only real failure? Failing to do anything at all.

Side Hustle Success Is within Your Reach – Right Now!

The truth is, side hustle success is easier than we allow ourselves to believe. And the obstacles in our path are smaller than we make them out to be.

Not convinced? That’s okay. I don’t blame you in the least, because it took going through the process myself to believe the words I stand by today. But at least let me try to show you how you absolutely can create a successful, profitable, fulfilling side hustle right now.

Check out these four simple keys to your side hustle success:

1. Be Sincere

In other words, be genuine. Be true to yourself and let that you-ness shine through the work you’re doing. It’s as simple as that and this one thing, if you can let it lead you through all your experiences professionally and personally, will always steer you straight.

2. Be Honest

In one respect, the Internet is like an infinite place in which to do business. We no longer have to compete because there’s room for everyone at the table; it’s an infinite pie and everyone can have a slice.

But in a difference sense, the Internet is a very, very small space where everyone will quickly learn your name and your reputation. If you lie about who you are or what you can do, the entire world is going to know about it.

Side hustle success can only happen for you if you’re honest, upfront, and willing to be transparent. Don’t use the fact that you might be separated by distance or a computer screen as an excuse to try and be less than virtuous 100% of the time.

Admit to mistakes when you make them. Ask for help when you need it. Acknowledge the fact that you don’t know everything all the time. Your honesty is key in building meaningful, lasting work relationships with quality clients and partners.

3. Be Confident

You’re establishing a side hustle because you want to pursue work that you enjoy and work that you’re good at. Own it!

You are good at what you do. You offer real value to others. You are totally rockin’ some socks off out there.

If you need a little help believing yourself when you say these things, consider printing off any praise you receive and putting it somewhere you’ll see every single time you sit down to work on your side hustle. That person probably didn’t take the time to send an email, text message, or call you up for no other reason than to blow smoke up your tail. If you did an awesome job for them – which you should be striving to do with every gig, every client – they are going to appreciate that.

When they choose to share and express that appreciation, that should mean a lot to you and go a long way to making you feel confident and capable.

Of course, there might be a slight hang-up here for some folks. I know I just said be honest – so how can you be honest about your confidence if you don’t have any?

Being honest doesn’t mean belittle yourself or fail to play up what you can do. When it comes to confidence, you might have to do a little fakin’ it ’til you’re makin’ it. This isn’t a lie. It’s the act of having faith in yourself and what you can do for someone else.

Work to develop genuine, real confidence in yourself at every turn. That confidence will make you happier and more sure of yourself. And other people are going to pick up on that in a very good way.

4. Be Nice

If you’re already being sincere and honest, it’s likely that being nice won’t be too hard.

Obviously, you’re not going to be intentionally mean or hurtful in your interactions with others. But there is a difference between being a decent human being and going out of your way to make someone else smile. That’s what we’re talking about here.

Remember to ask people how they’re doing. Don’t forget to bid them a good afternoon or evening. Say please and thank you. Ask if there’s anything you can do to help. Even when you’re dealing with clients, treat them as you would good friends. Be warm, inviting, friendly, and just plain nice.

For those of you who weren’t raised this way – remember, I was born and raised to be a sweet ol’ Georgia Peach/classy Southern Belle – it may feel like overkill. There’s no reason you need to over-exaggerate and be cloyingly sweet with your words. It should be within everyone’s capacity to address people by name instead of “hello Admin!” or to mind your manners when interacting with others, even in a digital forum.

Even if you’re not someone who regularly says “ma’am,” surely it’s within your personality to be kind. That’s the takeaway here. Be kind.

It’s common sense, my friends. Don’t let your communications be cold and distant. People want to connect with other people, so be accessible and eager to do what you can to make someone else’s day a little better than it was before they ran into you.

Side hustle success really can be this simple. Be sincere, honest, be confident, and be nice.

It doesn’t get much easier than that.

Do you have more questions about creating a successful, profitable, and fun side hustle? Be sure to leave them in the comments (and read up on the rest of the Side Hustle Shuffle Series!)

Other Posts in the Series:

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Shannon @ Financially Blonde

I think being honest is the most important key for success in side hustling and life for that matter. I had a successful career in sales for 10+ years because I was the most honest salesperson any of my client’s had. I lost business because I refused to sell what I didn’t believe it, but I made money down the road because my client’s remembered that. It really does pay off to just be upfront with people. It makes them want to work with you even more.

    Kali Hawlk

    I completely agree, Shannon. Being honest is going to help you develop lasting, quality relationships that are worth far, far more than whatever you could have gained out of being dishonest.

Tonya@Budget and the Beach

Good info Kali! I’m kicking myself for not side hustling earlier on in my career. :( I think the one thing I have discovered about side hustling is just flat out ask people. Ask if they need a babysitter, a dog sitter, computer help, organizing help, etc. I asked my friend the other day if he ever needed help with his corporate team building events and a couple days later I was hired to help at one. Boom! :) Asking goes a long way!

    Kali Hawlk

    Asking is key! It feels so hard to do at first, but once you start asking – and finding new opportunities, like your example! — it becomes an easy and obvious thing to do. People always need help with something, even if they don’t talk about it out loud, and you never know who might be looking to hire out help but just has no idea where to start.

The Phroogal Jason

Great points indeed. Having integrity is important. What’s the saying? Integrity is doing what you say you’re doing when no one is looking.

And it’s very true that asking goes a long way. There is never anything wring with asking. Ask for help. Ask if your assistance is needed. Ask and pay it forward. Not enough people ask. We all tend to assume.

    Kali Hawlk

    Love that quote, Jason – thanks for sharing! And thanks for sharing your thoughts on asking, too. Couldn’t have put it better myself :)


Having the confidence to put yourself out there really makes a difference. Being nice, sincere and honest easily puts you over half the people out there. Plus, you don’t want to start a business relationship off on the wrong foot by misrepresenting yourself. I love southern hospitality by the way; being a NY’er has made me a bit jaded!

    Kali Hawlk

    Glad you’re liking the Southern hospitality! I’ve found just being polite and remembering some basic manners goes a long way — so many people just don’t expect it so it’s a pleasant surprise for them.

DC @ Young Adult Money

I think confidence is the most important thing to nail down if you want side hustle success. When it comes to side hustles you are usually forced to “sell” whatever you hope others will buy – whether it’s your ability to write solid content, improve a spreadsheet, or even mow a lawn.

    Kali Hawlk

    Confidence is crucial! It’s also, for me, one of the hardest things to maintain on a regular basis. I think everyone has bouts of self-doubt, but believing in what you can do is so important if you want to find success with the work you’re doing (on the side or otherwise).


You’re killing it Kali. You have got to be one of the most motivated side hustlers I’ve ever seen. The amount of projects you’ve taken on, plus the fact that you’re writing is always freaking awesome, is just amazing! I checked out your freelancers site too and it looks and sounds great. I think you’re going to go really far with your content managing business!!

You’re the person I’d be taking side hustle tips from for sure.

    Kali Hawlk

    Alexa, thank you so much for the kind words! You’ve made my whole week :) I really appreciate you sharing that with me — you’re certainly one of the people who inspired me to take my side hustles to the next level. I really admire those like you who have built something from the ground up, and I want to be one of those people myself. Again, thank you for the wonderful comment. It means a lot to me.

Stefanie @ The Broke and Beautiful Life

Starting is the hardest part. All of the sudden the work comes flooding in and you feel like an old hat.


Good tips, Kali.

Being honest and sincere does go a long way, and can help you stand out in a crowded field. The best part is that if you make a positive impression, others will be happy to recommend you to their network.

Done by Forty

Great advice there, Kali. The problems are usually in between our ears, and they loom large enough that they often prevent us from starting anything new or scary. I’ve procrastinated on my side hustle for about a year now for the reasons you’ve stated…

Will, FQF

The whole being nice thing is soooo true. If I’m nice to a client but don’t know how to fix their problem, they will leave happier than if I’m mean and fix their problem in seconds. Honestly, I’ve kind of experimented with this…

I’m currently reading ‘How to Win Friends and Influence People’ by Dale Carnegie.


My first time here. Not a millennial but a boomer. I retired from law enforcement and now have a side gig. I do PI work for Indigent defense attorneys It’s rewarding and I make a little but the best is I am in control of my time. Many retirees chose to jump into another job for more money. I figure my time and freedom to chose is most valuable

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