The Entrepreneur's Dilemma

My reason for becoming an entrepreneur has never been to make money. It's also not about the status. I don't even like telling people I am an entrepreneur. After almost 4 years of not being employed, I'm still not used to saying it. The reason I wanted to become an entrepreneur is FREEDOM

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All the time in the world, but what to do with it?

My reason for becoming an entrepreneur has never been to make money. It’s also not about the status. I don’t even like telling people I am an entrepreneur. After almost 4 years of not being employed, I’m still not used to saying it.

The reason I wanted to become an entrepreneur is FREEDOM. When I did a review of 2023 I decided that my purpose in life is to maximise freedom, build a legacy.

  • Freedom to decide what time I get up in the morning
  • Freedom to decide when I stop working in the afternoon
  • Freedom to not work on a weekday
  • Freedom to work on multiple projects at the same time

The irony

For the last few months I have been busy building a web application that automates my primary business The Daily Wine. Long story short, the application basically automates the day-to-day tasks.

  • It places purchase orders from suppliers automatically each morning
  • Allows the person working in the warehouse to receive the purchase orders
  • Follows up when purchase orders are late
  • Tracks inventory and restocks when needed
  • Makes suggestions on which couriers to use to the warehouse dispatcher
  • And many more features will be added…

The great thing is, I can spend a week or two away from the business and it will keep on running, without any intervention from me. Which is great, and it has been one of my reasons for sharpening my coding axe in 2024.

The irony is:

  • This makes me feel disconnected from my business (which makes me anxious)
  • I feel guilty for having free time

Disconnecting and letting go

The problem is, if you have built a business - you are used to being on top of every single thing and making sure everything goes to plan. And I would say this is a good thing. If you don’t, arguably you’re business won’t make it. This has been a recurring theme for me in 2024, I have learnt so much from assistant. If you want to take your entrepreneurship journey to the next level, I believe you need to learn to:

  • Let go and trust other people to do a good enough job
  • Delegate tasks
  • Give constructive feedback

How to deal with free time

Having free time is not something most people every have to deal with - except for their 2 week holiday each year. You might be thinking: “Stop complaining, I wish I had free time”.

But free time can be a blessing and a curse. It all depends how you spend it.

When is the last time you just sat for 30 minutes with your own thoughts without scrolling through Instagram or distracting yourself with some reality show on Netflix? Try it - and you will realise that it’s not that easy.

When I became an entrepreneur I had these grandiose ideas of I will get up each morning, do journaling, exercise, eat a healthy breakfast, read a bit, watch a Ted Talk. Reality check, you can do all of these things and then it’s only 11am. What are you going to do with the rest of your day?

The other end of the spectrum

More free time = more time to work. This is my favourite trap to fall into.

To avoid dealing with the free time, you just fill your entire day, work on multiple projects at a time, never switch off and inevitable end up over working and burning out.

As I am writing this blog post, I am forcing myself to sit on a couch, on a Thursday morning and just relax for a bit. Why? Because I have been working non-stop for about 5 months (7 days a week), except an odd day here or there.

Dealing with shame

The weird thing is, people who don’t have the freedom to do what they want, often shame people who do. I don’t know if it’s a knee jerk reaction from their side to try and make themselves feel better. But often I receive comments in the line of:

  • You only wake up at 7am? I start working at 6am! (I struggle to stop working and switch off)
  • Not everyone are so privileged to work for themselves (It’s a privilege I risked everything for and got into loads of debt for)
  • I’m not a successful entrepreneur, I only get a salary (most times I earn less than what I could working for someone else)

Striking the balance

I believe it is possible to strike a balance between work and play. I have not achieved it yet, but I am working on it.

It’s not a bad thing to fill your free time with activities, but I think a good strategy is:

  • Fill it with more activities that focus on physical and mental health.
    • Exercise
    • Healthy eating
    • Walking on the beach
    • Watching sunsets
    • Playing with your pet
    • Working in the garden
    • Reading a good book (not a business book, some fiction)
  • Spending time with family and friends (Call your parents!)

And you are allowed to work

Remember, working is what bought your freedom, so you are allowed to work. But focus on doing high-leverage work, that buys you even more time and freedom do to all of the good stuff above.


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