Starting a freelancing business is hard. I'm not gonna sugar coat it – actually, the reality is, stepping out and doing something different is always harder than staying in your full-time job, which is why I guess so many people don't do it.

Until something clicks or something happens to make them decide to step left instead of right.

That's what happened to me. As I mentioned in this interview with Elisa Doucette, I didn't think about starting a side hustle until about 2009. Up until that point, I'd been happy to step right.

So what changed?

I can't really pinpoint a definitive date or time that I made the decision that I wanted to do something else with my life other than work for someone else. It was more of a feeling. A feeling of discontent with my work, feeling stuck and not being able to do the things I enjoyed doing.

Essentially, I felt like my job was holding me back.

If you want the full story, you can hear more about my journey in the interview I did with Sean Ogle from Location Rebel below plus I've talked about it on my blog before as well.

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5 Lessons Learned Working Full-time & Starting a Freelancing Business Start a freelancing business

Let's fast forward to my side hustle, the one I started part-time while I was still working my normal day job.

I worked 40++ hours per week at my day job, started a relationship, and had a pretty active social life. I didn't really have a ton of spare time. What I did have was a desire and drive to get out of the job I was stuck in. I made the time because it was that important.

As you can imagine, there were moments when I resembled a juggler more than a hustler. There were times when I just wanted to chuck it all in and just take the easier way, ie, keep stepping right and stay in my job.

[Tweet “what I did have was a desire and drive to get out of the job I was stuck in”]

Then I had an enlightening conversation with my boss. She told me that I would always stay in the job I was in because I was so good at it. Unless she retired, there was no room for me to move.

After that conversation, I was determined to make my own path.

As a result of that conversation and everything I learned, I wrote a book called Side Hustle Blueprint: How to Make an Extra $1000 in 30 Days Without Leaving Your Day Job. It will help you figure out your side hustle idea and how to get started.

Below are the lessons I learned during the 10 months I was working full-time and hustling on the side.

They are lessons that I hope can help you too, particularly if you are thinking about doing the same thing!

Lesson 1 – Schedule Shit In!

I prided myself on being a pretty organised person. However, organising your work life is pretty simple because you're at work for a set number of hours and you schedule meetings within that time, right?

Add another layer with your side hustle and things can get pear-shaped pretty quickly. I remember having three separate calendars at one point. One for work, one for my side hustle and one for my social life – and none of them ‘talked' to each other! It was a little scary.

So the lesson here is – make sure you have one calendar that reflects all of your commitments. This way you won't miss your normal work deadlines and you also won't drop the ball when it comes to your side hustle and personal deadlines.

[Tweet “make sure you have one calendar that reflects all of your commitments…”]

I use Google Calendar because I can have multiple calendars showing at any one time and I can colour code them.

When I was working full-time, this allowed me to quickly see where I had room to move things around and where I didn't.

Lesson 2 – Under Promise, Over Deliver

I like to provide as much value as possible to my clients, but that can lead you down a scary path to dropping the ball.

I quickly learned that under-promising and over-delivering, was much easier than trying to provide the sun, moon, and stars.

Of course, you can and should over-deliver, but you don't have to go overboard.

Think of simple things you can do to the job you're working on that will provide value to the client. This is over-delivering. You could get the job back to the client well within the deadline, which would be classed as over-delivering.

Don't put yourself under unnecessary stress – particularly when you're still working your full-time job. You need to be able to balance both and the best way to do this is to under-promise to your side hustle clients but over-deliver in ways that they may not expect.Capture Convert Captivate Workbook

If you need some ideas on what to do or what that can look like, I cover that in my book Capture, Convert, Captivate.

This all ties into the first lesson – making sure you schedule things in. If you've got your scheduling sorted, then over-delivering should become second nature.

[Tweet “Don't put yourself under unnecessary stress!”]

Lesson 3 – Use a Pen Name

In the first few months of starting my side hustle, I used a pen name because I was worried that my boss would find out what I was up to! I did not want to tip her off in any way, shape, or form, so I used a pen name when setting up my profiles on sites like Upwork.

I used “Lisecnz” because it was close enough to my name but not something that would come up in a Google search attached to my ‘normal' name.

If this is something you're worried about, I cover this in-depth in my book Side Hustle Blueprint: How to Make an Extra $1000 in 30 Days Without Leaving Your Day Job!

There is absolutely nothing wrong with using a pen name. Sometimes it just makes life a little easier to separate your work life from your side hustle life. At least in the beginning.

Once I was confident that my boss wasn't Googling me all the time (because in reality, why would she even bother?!), then I changed my profiles to be Lise Carter (my maiden name).

Do what feels right for you.

Lesson 4 – Do One Thing

It's a very bad habit of mine that I typically have at least 2-3 projects on the go. This was no different when I decided that I wanted to work for myself.

I decided that my side hustle would be a mixture of skills: Search Engine Optimisation, SEO Writing, and Social Media Management.

Um, I don't know about you, but trying to build a skill across three different areas is pretty challenging.

I quickly learned that I couldn't manage all three well. So I decided initially to just focus on search engine optimisation. About 4 months into that, I decided that keyword research and website analytics were not my thing. So I then changed to SEO writing.

This is where I really started to thrive.Cultivate Your Hustle Workbook

So if you're starting out with a side hustle, make sure that you just choose one skill to hustle with. Don't make life hard and try to throw your hat into many rings, it will only lead to you pulling your hair out!

If you need help getting clarity on your one thing, check out my workbook, Cultivate Your Hustle. You'll find exercises and tools to help you get clear on what your side hustle looks like.

[Tweet “…just choose one skill to hustle with in the beginning”]

Lesson 5 – Take Time Off

I know that a lot of people tell you to hustle like crazy when you're starting a side gig. But I found myself getting really overwhelmed with both work commitments and side hustle deadlines, not to mention spending time with my boyfriend and friends.

At one point, I was running around like a headless chicken and thought to myself, “why am I doing this?”

Don't forget to schedule in time away from all your work stuff, both your normal day job and side hustle work.

You need to recharge your batteries and unless your Superman, that's not going to change anytime soon.

This lesson was a hard one for me to learn. Many weekends were spent working at my desk when I'd rather have been at the beach.

I had to remind myself that I had choices. I did not start the side hustle to work myself into the ground. It was meant to give me options. I got really clear on my why. I contribute a lot of my online business success to that one thing.

Find your why. It will drive you when other things are pulling you off course.

Once I realised that, I just scheduled in time off. This became much easier to do once I quit my job of course. You can and should still do this even when you're still working full-time and working your side hustle part-time.

[Tweet “This lesson was a hard one for me to learn…”]

Stepping to the left is not easy, but if it was everyone would be doing it. When you’re clear on what you want to accomplish–the bigger picture behind your decisions–it becomes easier to follow the path to your bliss.

Action Step

Have you experienced any of the above? Do you have any lessons to add to this? Leave your thoughts in the comments below!

Ready to join a community of like-minded people? Consider joining The Empowered Hustle Community if you haven't already!

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!

    2 replies to "5 Lessons I Learned Working Full-Time and Starting a Freelancing Business"

    • Bella

      Loved this!! Lots of similarities to what I’m going through ? add a layer of “I never think I work hard enough” to that list and I have a million things going on lol. Finally got a physical planner to separate some stuff from the computer too (would love a blog post about how to balance so much working on the computer: hobbies and work and side hustle all on a computer it can be a LOT) ?

      • Lise Cartwright

        Amen to physical planners Bella! I love me some online planning, but cannot go pas a physical planner for writing down all those thoughts that come up! Great idea for a blog post, adding it to the list 😉

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