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5 Deadly Mistakes I Made in My First Attempt at Self-Employment and How You Can Avoid Them

Wessam is a successful entrepreneur with a story behind her rise. It is not a secret that in order to build a successful business, you need to have stability. That includes your personal life – which to some is a secret perhaps until you learn from life’s lessons first-hand. Follow Wessam’s story as she bounces back from incredible challenges to tell her story.

“This is not the life I subscribed to”, I thought to myself as I reflected on my 9 to 5 job. My job was frustrating. I grew increasingly tired of working a 9 to 5 job, handling office politics, and dealing with abusive managers. I started to toy with the idea of working for myself.

What inspired me to consider self-employment was the freedom I crave and the autonomy to dictate my schedule. I was so excited to start something new. Little did I know that the journey would be far from smooth. I had no idea what I was doing then. I made a ton of mistakes. The following are some of the deadliest mistakes I committed along the way.

I explain them below so you will not have to repeat them if you ever consider self-employment. So, let’s dive in.

How Stable Is Your Personal Life?

Venturing on your own in any way, shape, or form is not for the faint-hearted. It requires a lot of grit and support. You know you are ready for this step when your personal life and relationships are stable. I started my first business attempt during some serious marriage troubles. It was my way to escape facing my issues. Later on, the troubles escalated to a divorce.

I found myself in a situation where I had to manage divorce legal issues, emotions, money, and kids all while running a business. Needless to say, the business did not take off. I was too distracted to focus on it. Sheryl Sandberg was right when she said “the most important career choice you will make is who you marry.”

 Don’t fall into the same trap. Get your personal life sorted out first and foremost before you jump into any form of working for yourself.

If Content is King, Context is Queen

Every piece of advice you hear and read online (including mine) is useless without understanding the context. Everyone is focused on promoting their services. It is up to you to decide whether this service suits you at this particular stage of your journey or not. For example, people all over social media will claim they made ‘X amount of money’ in a few short days.

What is often missing from this narrative is the big picture. What they don’t tell you is the amount of prior preparation, failed experiments, and trial and error that preceded making this amount of money. When you consider all the above sacrifices, the story may not sound as attractive as it initially did.

The lesson is simple. What applies to someone’s case may not apply to another’s. Stop listening to every piece of advice and start thinking if the context: if the advice applies to you or not.

Leaving your 9-5 job pre-maturely

I was guilty of this one. My self-employment journey started with me approaching training companies. I pitched myself on how I can develop and deliver world-class training that will bring them a consistent stream of corporate clients. When some training companies responded to my offer and started to hire me, I got too excited that I submitted my resignation in the following few weeks.

I thought I made it. But I was wrong. Building a sustainable business that brings in consistent income every month takes time. Your 9-5 job becomes more important than ever if you are starting a side project. Your 9-5 salary is what will finance your passion project expenses until it can cover itself.

Without this level of security, your side project will never see the light. Don’t leave your job at the early sign of traction. Leave it when the income generated from your side project is big enough to replace your current salary, not in a single month, but consistently.

Blowing out your health

I did not realize how big this one was until I found myself bedridden in the hospital, unable to walk to the washroom. During a divorce, I ignored my health or took it for granted. I stopped:

  • Eating healthy.
  • Moving or doing any kind of workout
  • Actively managing my stress
  • Wearing nice clothes or makeup

In a nutshell, I neglected my well-being and was on the verge of collapsing. The accumulation of all these wrong habits took a toll on my health and sent me to the hospital for weeks. What helped me recover was exactly the opposite of the above list. I now have deep respect and appreciation for entrepreneurs, like Matt Gray, who prioritize and teach health as an integral part of their entrepreneurial journey. If you do not take care of your health, nothing else matters. PERIOD.

Redefine what is cheap vs. expensive

In 2011, my first website was hacked. I lost all the stored data on it. My work stopped completely for weeks until I paid someone to clean up this mess. It was a nightmare. I learned the lesson the hard way. If your website is going to be a major part of your work, you need to pay to secure it.

You also need to pay for backing up the data on the server. The keyword here is PAY. Free options won’t serve you in this case. This applies to everything else in your business. I know when you are starting you are probably bootstrapping. But you need to change your mindset when it comes to spending money.

Stop seeking things that are free or cheap. And start thinking about:

  • What value you’re getting in return
  • What loss you will have to deal with in case you choose not to pay

Some services, if you pay for them now, will save you a ton of money and effort in the long run. That is not what you should call an expensive service. Doing everything yourself to save now can cost you headaches and waste your time later on. Cheap and expensive are relative. They are not about the money you pay. They are about the value you get compared to what you paid.

Final Thought

Self-employment can be a very exciting journey. It can also be a nightmare if you do not know what you are doing. The top lessons I learned in my journey are:

  1. The stability in your personal life can make or break your business
  2. The context of any advice matters. Do not ignore it.
  3. Don’t leave your job until you can generate enough income to replace your salary
  4. Take your physical and mental health seriously
  5. Be willing to invest in services that save you time, money, or effort in the future.

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