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by richsin 4270 days ago
As someone who turned 30 recently and would classify my 20's as 50/50 win-lose, I feel I can add to this.

I am single, however family is becoming increasingly important, but to each his own. As much as I dreamed of being a playboy entrepreneur in my 20's, I started tuning in to what I really want, and it's scary.

How will I still achieve my dreams and embark on something as demanding as a family? Feast or Famine is not an option amongst other things, but this is not about relationships, it's about career.

My recent job search was eye opening, I decided to get back into the working world after 8+ years and here is what I have boiled it down to:

1. My biggest mistake while I was an entrepreneur was failing to develop a role for myself. Although you may have to wear many hats in your day to day, you should always try to become an expert at what you're good at. For example, I did marketing and development, pretty good at both, but when looking for work I did not have much of a portfolio and to be very honest, I felt like a hack. Stay prepared and be able to demonstrate and prove your ability at any given time.

2. Failure happens. The delicate part is not looking desperate. Lifestyle change, sparked interest in a new industry or just simply making the next step in your career are all good reasons for transitioning from founder to employee. However, I felt there was some judgement passed on a few occasions. Forget them, it's not worth it.

3. Going out and taking a swing at your dreams deserves a lot of respect. There is so much mediocre in this world that an attempt to do something substantial in your life is not crazy.

4. Being a founder is a thankless job. There is no love until you become successful, or at least look like it. Forget what society thinks, you will almost never get the response you want when you make this decision.

5. Optimize, automate or delegate. After years of overworking, deferring life, missed encounters..... It's not worth it. Having a family may make you a better founder because it gives you boundaries. Respect your time, set your hours and give it your all when you are working at it. Nothing is perfect, but it's amazing what you can achieve when you have 8 hours to GTD.