Many of us crucify ourselves between two thieves – regret for the past and fear of the future.
Fulton Oursler

He who is not everyday conquering some fear has not learned the secret of life.
Ralph Waldo Emerson


1) Identify how you would approach life differently if you never had to worry about money and were not afraid of failing.

2) Identify what is the worst possible scenario that could happen if you were to approach life this way.

3) Identify what steps you could take to work your way out of this situation.

Goals: Realize that fear is probably keeping you from some good things and even if everything goes horribly wrong you can easily work your way out of it.

One of the truest things I found in Tim Ferris’s book (4 hour work week) was the idea that most people would rather stay settled in an unsatisfying situation than face the fear of change.  If I were truly unafraid of failure I would definitely try countless new things and seek out adventure.   And I think thats the whole point.  To seek out challenges rather than stability.  To find things that interest and excite you rather than hoping to avoid difficulties and things out of the ordinary.  When thinking about the “worst case scenario” I found it interesting that I didn’t really fear losing money (probably because I don’t have much to start with).

What I really feared was that if I were to take a risk I could possibly end up more stuck in a situation that I enjoyed less.   But I think that as pretty much anyone goes through this exercise they are likely to realize that the worst case scenario is not too likely, in fact it’s unlikely.  And the more realistic you become the more you realize that even if you were to take a risk you could probably work your way back to your current situation fairly easily. Here’s what our worst cases look like.


1) What is the absolute worst that could happen if you did what you are considering

  • R – i would lose $1000-2500 dollars, get scolded at work for being distracted, seem like an idiot, babble about this to people, end up with nothing, waste lots of time and energy
  • B – I could quit my job and always regret it because I couldn’t find another that I liked as much.  I could blow all my savings and regret not being able to buy a house or provide for family in the future?  I could leave the country and be bored by myself (possible die) and feel like I just wasted part of my life and time.

2) What steps could you take to repair the damage or get things back on the upswing, even if temporarily?

  • R – work extra freelance/craigslist gigs, sold stereo and tv, focus more on work productivity instead of financial freedom productivity, not babble
  • B – sell body to the night. apply for minimum wage jobs until a teaching position opened up.  Move in with mom or dad and look for teaching jobs around country.

3) What are the outcomes or benefits of more probable scenarios?

  • R – figure out financial success like books report and people have done before me, gain some life experiences people don’t have, actually make money and or have a start-up, meet tim ferriss like my brother claimed he did, travel.
  • B – start a product and make extra money.  Have more fun and enjoy each day more.  Not feel like I am wasting time.  Actually meet people.

4) If you were fired from your job today what would you do to get things under financial control?

  • R – sell everything except my computer, make…umm $2000 live off credit cards and craigslist jobs until i got another consistent IT gig
  • B – look for a waiting job or something until I could get back into teaching.  Try to start own business.

5) What are you putting off out of fear?

  • R – spending money on ideas i think will work. putting more money into savings because i think i’ll need it now. putting myself, my name, my face out on websites and products in case they fail.
  • B – meeting people of the opposite gender.  traveling and being alone.  doing anything new.

6) What is it costing you to postpone action?

  • R – its costing me experiences to look back on. the possibility of not living life, but just being another american robot working for a weekend. time and fun in exchange for dull security, thats not even secure.
  • B – Wasting time.  actually living the way I am afraid of living. Feeling bored, trapped and alone. Wasting time.