The 5 lessons from 5 years of side hustling I wished I knew when I started

Hi there,

I recently returned to Medium after a break of 4 years. Sometimes I wished I stuck with it when I started in 2018. I was gaining traction, earning some money writing there, even becoming a top writer in a couple of topics. But then I left because I felt my results weren't big and fast enough. Or maybe I got distracted by the next new shiny object. I really can't even recall.

Here are 5 lessons from 5 years of side hustling I wished someone shared with me when I started.

I hope this helps you save the time and frustration it took me to finally get this.

1. You don’t need the bells and whistles to start.

Throwing more money doesn’t always solve the problem. When you’re starting out, it can feel overwhelming because you think you need to have all the things. You really only need to have a means to share your ideas with one person, then the next person, and the next. Social media is great for this, but so is a forum, a special interest group, or your friends. As you talk about your idea and what problem you solve, you get clearer about what you do, and how and who exactly you help.

What you can do:

Tell as many people as you can about your service or product. Get them to refer and share with their friends and network. Collect the feedback by assessing if anyone takes you up on your offer. If they do, you know you’re onto something. If they don’t, ask what they want instead and how you can help them with it.

2. You can help someone even if you think you’re a beginner.

Lack of self confidence is one of the biggest obstacles to learning and getting results faster. You feel like you’re not qualified or experienced enough to teach someone else. So you spend your time getting all the information, certification after certification, hoping to bolster your knowledge and wisdom. The fastest and easiest way to get qualified and experienced is to help someone. You can help someone from where you are right now. There’s always going to be someone who knows more than you, and another who knows less than you.

What you can do:

Help one person who knows less than you. Learn from those who know more than you. Repeat this to get the experience and wisdom you seek.

3. Keep it small and simple. Most importantly, stick with it as you continue refining.

When I started side hustling, I did all the things. Building automations in my emails, launching online programs, coaching programs, worrying about which payment processor to use, researching all the different learning platforms and so on. Looking back now, I realised, a simple, free platform like a Google Document, Sheet and Slides were all I needed. Get a free Zoom account and start talking to and helping others. We often get distracted by all the unnecessary things we think we need to be successful. The most important thing is to stick with it, learn from what you’re doing, iterate and improve along the way. Getting into too many things complicates matters and makes it difficult to stay consistent.

What you can do:

Strip all the unnecessary distractions and get to the heart of who and how you help. Then just help them.

4. You need to have a strong reason to stick it out.

Whatever you want to create will take longer than you expected to materialise. This means you need to keep the reason why you started a side hustle front and centre. When I started a side hustle, it was for the very practical reason to make more money and pay off debt. Making the money I wanted took a lot longer than I expected. So I had to ask myself why I wanted to pay off the debt? Here’s what I came up with:

  • I wanted to be free from having a heavyweight holding me down, i.e. the debt.
  • I wanted this freedom so I could provide a better future for myself and my family, like a good education for the kids and experience fun and adventure through travel.
  • I wanted to know that my family and I would be ok, even if I was let go from my job.

In other words, I valued freedom, security, and adventure. They were my reasons for sticking it out even when it’s taking longer than I expect for my side business to be at a level where I want it to be.

What you can do:

Take some time today to figure out why you want to start a side hustle. Go beyond the superficial and obvious answers of financial or time freedom. Why do you want those? What do they represent or do for you? Keep them front and centre especially when you feel like giving up.

5. Learn to love the plateaus and the process of practice.

Since things will take longer than you expect to materialise, besides having a strong reason for sticking it out, you have to learn to love the process of practice and the plateaus that come along with sticking with the practice. We mistakenly expect progress to be a linear upward progression like the perfect graph you see below. Somehow, even though intellectually we know this isn’t how it works, subconsciously, we still expect it to be like this. It's why we get upset, disappointed and disillusioned when things don’t happen as we expect. The reality is, we’ll see some progress, and after that it will feel like nothing is happening and we’re plateauing. How we get through this 'boring' or 'it's not working' phase when it feels like nothing is happening and we’re stagnating makes all the difference.

What you can do:

Instead of giving up, use this time to deepen your expertise and gain mastery through practice and repetition to prepare for the ascent to your next level.

Final thoughts

5 years is a long time. But then again, it was the path I needed to take to learn the lessons. I realised there are so many paths to success. It's entirely up to you whose model you want to emulate. Better still, mix and match to come up with your own.

These days, I deliberately keep things very small and simple so I can stick with it in the long haul, even when it seems like nothing is happening.

I hope you give these 5 lessons a shot. It's how I'm gradually growing my audience, in a very enjoyable, meaningful and sustainable way as I apply these lessons myself too!

Here's to your success!


P.S. Want a step-by-step guide to achieve your goals and get anything you want with calm, clarity and courage? Sign up to my free 5-Day email course to learn how.

Sharon Singh Sidhu

Ready to rewrite your career story? Get practical strategies for real-world success to thrive in your career while building your dream.

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