You will hear and read a fair amount about how tough the first year of business can be or that if you make it through the first year, you’re over the highest hurdle.

Nope. Nope. All the nope!

The first year is filled with adventure, novelty, bright eyes, and bushy tails. That all wears off in the second year and reality hits and, unlike a toddler, who may naturally grow out of this phase (you hope), you’re the only one who can teach your business how to run. Imagine being a two-year-old kid and teaching yourself how to walk and talk. Now throw in some quantum physics and that’s pretty much how entrepreneurship at this stage feels.

I have a business stumbling out of its second year as well a business that’s about to move clumsily into its second year, and here’s what I learned about the Terrible Twos.

You test the processes

Just as a toddler finds their feet and explores the beautiful and dangerous things that life has to offer, a business owner starts defining their vision. Your first year is spent trying it all and experimenting with various products and clients. Attempts to start specifying these can lead to a mountain of uncertainty and frustration. You will fail. You will spit some ideas out and you will hold on to some like a comfort blanket. You will fall on your ass and you will get shouted at. It’s all part of finding your voice, your personality and your USP.

Cash flow

You learn patterns and, by this stage, many fixed costs such as rent, salaries, and software may be firmly in place. During the first year, you’ve still been out of the job market for a short enough time to go back. The second year feels more committed. You’re way outta the womb now and need to negotiate how to get that treat for doing good.

You throw tantrums

The entrepreneurial journey will lift you to your highest highs and push you to your lowest lows. You will be taken on an emotional rollercoaster that you didn’t sign up for. This is because you’re forced to do and be it all. As your business matures, you’re wearing all the hats, from the ops lady to the tea guy. It’s uncomfortable and messy, and can make you feel inadequate. But the triggers that caused your tantrums become easier to manage.

You can’t do it all

In your first year, you’re wearing all the hats – feathers and all. This quickly becomes unmanageable as your job, as a business owner, is to steer the ship, not row the ores. This may mean letting go and putting trust into staff or outsourced suppliers. No matter how stubborn the toddler is, they will always need help climbing onto the jungle gym at some point.

So how do you get through this phase alive?

Put systems in early

Whether you’re running an e-commerce platform or a dry-cleaning business, monitor and take note of every step in the day-to-day running order of your business. From the first contact with the client to closing the deal, as well as all admin processes such as human resources and finances. This may seem totally pointless in the beginning as you can handle it all, but once you start hiring people to take over certain roles, it will help to hand over a deck of roles and responsibilities. Trust me.

Speaking of trust…

Learn how to do just that – trust. Delegation sounds like such a simple theory; order people around and it’ll get done, right? It took me too long to allow my team to get on with a project without providing my input (What’s an entrepreneur without a little OCD?) I had to remember that I had hired this team for a reason. Be clear on the objectives and ensure they are equipped with all of the correct tools to deliver, and then provide feedback on how to improve for the next order or project.

Pick your bottom lip up off the floor

Sure, it’s your business and you design it the way you want, but that doesn’t mean that everyone is going to agree with you or what you do. Craig Rodney gave a talk at a conference a few years back where he spoke about learning to fall in love with the hate. He was talking more from a consumer-brand perspective, but this can be applied across the board. Look at the critique you are receiving, kick your pride to the side, see the value in it, and improve your offering.

Be adaptable

You don’t know it all and you still have a lot to learn. The second year will provide you with more perspective on your business as well as a more objective view. Take 15 minutes every day to research the latest trends in your industry then write down five new ideas that you can take to clients pertaining to those trends.

If you’re not making money, move on

Yes, that’s right. I’m suggesting giving up. Be honest with yourself. If you’re two years down the line and still not making money or seeing a future where profit is imminent, start over or start something else. Learn to crawl.


This notion of entrepreneurs needing less sleep to increase productivity needs to end. If you’re overtired, you will forget to complete tasks and feel like a drunk toddler.

Lastly, and most importantly, never forget how far you’ve come.

You have a business that has survived possibly one of its most difficult stages. Yes, there’s a lot more to come, but never forget to take time to reflect and give yourself a pat on the back for all you have achieved so far.

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