Which is Riskier?

Going All In When You Are in Your Early Twenties

Gary Vaynerchuk advocates for taking big risks when you are in your early twenties. He has three main points:

  1. You can afford to lose because you have time to recover.
  2. You are in the best position to work 18 hour days, eat awful and grind.
  3. You do not have significant barriers e.g. a family to support.
“This is the time to be massively risk orientated.”

I fit the target consumer of Gary’s video reasonably well. I recently started a business, turned twenty and entered my final year of university. I absolutely want to make the business work, but have trepidation around the practicality of relying on a new start-up as a source of regular income. Today I debated how I should approach the coming year as I need a regular source of income, but I also want to remain dedicated to my new venture.

Two Perspectives

In this debate there are really only two sides.

  1. Continue to study, work part-time and run the new business.
  2. Continue to study and run the new business.

The first perspective seems sensible. I work to be able to pay rent, power, internet and eat once or twice a week. I then pour whatever left over time I have into my new venture.

The second perspective is significantly more risky as I would have to rely on the income from the business to pay for my rent, food, power and internet.

However, this does not mean the second perspective would be the worst choice.

A Psychological Stand Point

Choosing the second option does not offer security. However, it may offer better results for my business.

Being able to eat, sleep indoors and use modern technology are things which I care about and therefore they motivate me. If I choose the first option, I am guaranteed these luxuries regardless of how my business is going. Conversely, if I choose the second option, whether or not I get these luxuries is completely determined by how my business is going. In which circumstance am I most likely to work my ass off to get the business off the ground? The circumstance where I choose the second option.

Yet, I am still drawn towards the first.


Is it actually riskier for me to take the first option? If so, does that mean I am risk orientated for being able to weigh this up and still choose option one?

You tell me.

Fraser McIntosh and Callum Herries write original content. I turn their advice into dialogues about my life. This is dialogue #18

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