Congratulations, you're starting a side hustle! You’ve decided that you’re going to start a side business and you’re excited. You can’t wait to get started.

Starting a side hustle can be a little overwhelming, particularly when you delve into everything that you need to get done just to ‘open the doors.’

When I got started, I didn’t do a lot of research. I’m more of a “jump straight in and figure out the details kinda gal…” but that doesn’t always lead to success, and it definitely makes kicking off a new business a lot harder than it really needs to be.

You know what I wish I'd done? I wish I’d kept things simple. I wish I’d done a bit of research so I knew what I was getting into, instead of having to flounder around and figure things out as I went.

I don’t want this for you.

Of course, if you want to do things the hard way and figure them out on your own, be my guest… this post won’t be helpful to you so you should stop reading here and go back to what you were doing… or you might find these blog posts more useful:

If you don’t want to do things the hard way — if you’d rather learn from my mistakes — then by all means, continue reading! Getting a side hustle up and running doesn't have to be hard…

Listen to this blog post instead!

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5 Things I Wish I’d Known When I Started My Side Hustle

5 Things I Wish I'd Know When Start a Side Hustle #sidehustle #workingfromhome

#1: How hard it was going to be to find my first client

Finding clients is actually fairly easy, if you’re doing something that you’ve got experience in, but if you’re starting out in a skill that you don’t have experience in, well, that can make things a little tricky…

My first side hustle was in SEO Consulting… as you can probably guess, I wasn’t overly successful in it.

This type of skill can be difficult to get hired for on sites like Upwork, because clients are generally looking for a ton of experience in the person they wanna hire, which is completely understandable.

So how do you find your first client if you’ve got no experience? This was the question I faced when I got started.

Here’s what I did to secure my first SEO client (shortly after this, I realised how much I disliked this type of work and switched to freelance writing):

  • Setup my profile on Upwork
  • Offered my services for free in exchange for testimonials that I could share in my Upwork profile
  • Reached out to my network to see who was on Upwork that could hire me for a few SEO related jobs, at low cost
  • Got 2-3 jobs on Upwork to increase ratings
  • Landed my first proper paying client!

All of this took about 4 weeks to achieve.

After that first initial client though, I learned that I did not enjoy SEO consulting… too many unknowns and clients who don’t understand how SEO works can get a little shirty with you if things don’t go how they want them too… Frustration City!

I quickly switched to freelance writing and pretty much did the same thing to increase my portfolio and add testimonials. It didn’t take long to get a client on Upwork from there.

I also looked at connecting with SEO consulting companies as well who might have been looking for writers, but didn’t enjoy the cold emailing aspect.

Upwork was definitely my preference.

Key Takeaway: Understand that it can take a bit of effort to secure your first client, but if you offer your services for free in exchange for a portfolio mention and a testimonial, this can really help increase your chances of landing that all important first paying client.

#2: The importance of scheduling your side hustle

Why you should schedule a side hustleFor someone who's as organised as I am, I really didn’t give this much thought, and it nearly cost me my freelancing business…

It’s hard to switch to being the boss of your side hustle when you’re working 8+ hours in your day job as an employee… it’s a bit of a mindset switch to being the boss and with it, comes a ton of responsibility… namely you’re in charge—of everything!

Initially, I didn’t schedule in time for my side hustle, I just fit it in around everything else… fast forward 4 weeks into my side hustle and I had missed my first client deadline because I hadn't added it to my calendar.

I wasn’t working on my side hustle every day, so it was easy to miss these things…

I learned the hard way how important it is to schedule your side hustle hours and keep track of deadlines.

Thankfully, I was able to chat to the client and explain the situation. They allowed me an extension and it was at this point that I decided to setup my Google calendar with my side hustle hours and to give myself a 24 hour buffer before a deadline… so this meant that my deadline was always 24 hours before the clients, just to allow for any life issues getting in the way.

Key Takeaway: Schedule your side hustle into your calendar and include a 24 hour buffer for deadlines so that you’re not scrambling if something does go wrong and you’re delayed.

#3: How important a domain name was going to be

While you don’t need to have a website set up initially, it does help make you look more professional and also encourages people to check you out and reach out to you via your contact page.

What no-one really tells you (because it is about personal preference) is that if you choose a domain name now and build your site, it’s bloody difficult to rename (rebrand) it further down the track!

Yes, you can easily change your domain, but if you want to keep the same site, it’s a lot of technical work in the backend to make the change and can cause a major headache from an SEO perspective.

While you shouldn’t get too hung up on a domain name, it does make sense to go with your name… I wish I’d done that. It’s a lot easier to stick with your name because you’ll always have it!

So if there is one thing I could recommend, definitely register your name or a variation of it, then even if this side hustle doesn’t pan out, you can still pivot and go in another direction but keep your website and domain name the same 🙂

Key Takeaway: Register your name for your domain name, particularly if you’re just getting started and aren’t sure if this side hustle is going to be what you truly want to do.

#4: How many questions I’d get from friends and family

How to handle questions from family and friendsHonestly, you’d think I was joining the circus by the reactions of my friends and family to the news I was starting a side hustle! You can only imagine what was said when I quit my job and went full-time… but that’s a story for another day!

Fielding questions from well-meaning friends and family about something you’re just getting started with and aren’t 100% sure on yourself — can leave you feeling a little confused and more than a little annoyed… at least that's how I felt in my case.

I wanted people to be supportive and happy for me, but instead, a lot of people wanted to know all the nitty gritty details… and I didn’t have the answers to those probing questions because I was only getting started.

The worst people were generally those who were in corporate jobs getting paid lots of cash… they couldn’t understand why I would even want to do this, and wanted to know all kinds of things, like how many clients I had, what the numbers were in terms of conversions, etc.

Dealing with these difficult conversations can be a right pain in the ass, but I found the best way to handle these questions was to simply smile and deflect by asking them a question about themselves… or depending on the person, I’d say that it was still early days yet and that I didn’t have the data…

I’m a fairly open person, so I guess I opened myself up to this type of reaction, but at the same time, it also helped me get clearer on how I wanted my side hustle to be viewed and what direction I really wanted to go.

Key Takeaway: Don’t mention your side hustle if you’re not prepared to answer all the probing questions that tend to follow!

#5: How important having access to a community was going to be

Starting a side hustle shouldn’t be done alone.

If possible, get access to a community of like-minded people… it’s the only way you’ll stay sane, trust me on this one.

It worked for me. I felt very isolated when I started my side hustle, because I was living in Australia and no-one I knew was doing anything like this. I had no-one to talk to about the questions I had… until I plugged into the Location Rebel community. The forum was amazing and still is to this day.

Find a community of people who are doing what you’re doing and connect with them. This could be inside a Facebook Group, a LinkedIn Group or you might find a mastermind of people willing to let you into the fold.

Here's a quick list of the current Facebook Groups that I'm in that are active and super supportive. Before you jump in and join, make sure you check out the description for each one, often they require you to join their email list first: is also another great way to find like minded people in you local area.

You need these connections to stay sane, it can be extremely isolating when you’re just getting started and having a community or people that you can reach out to when you have questions is life saving… even more so when you decide to go full-time in your side hustle!

Key Takeaway: Find a community of like-minded peeps and connect with them on a regular basis for your own sanity.

Starting a side hustle was one of the most rewarding things I’ve ever done, but it was also one of the most stressful times in my life. Avoid the stress and learn from these five areas I wish I’d know about so that you can move forward faster and be in profit sooner!

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Lise Cartwright
Lise Cartwright

Founder of Hustle & Groove and your creative business strategist. If you want to get notified of new posts just like the ones you see here, then make sure you join the awesome H & G community — Join Now!

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