This document summarizes a risk and confidence workshop led by Kate O'Reilly. The workshop focused on overcoming fears of taking risks, building confidence through everyday actions, and providing exercises to help participants identify risks worth taking in their own lives. Key points included establishing the group's principles, telling stories of building confidence through small assignments, and five suggested risks participants could take immediately to increase their confidence, such as trying a new physical activity or putting themselves out there for a job they feel is beyond their current abilities.

1. Risk
Workshop
KATE O’REILLY // @CLEVERKATE
#unleashed // #40forward

2. Hi, I’m Kate.
The helmet brand is acutely accurate.

3. -Someone very smart
“Life begins at the end of your
comfort zone.”

4. Let’s recap, shall we?
KATE O’REILLY // @CLEVERKATE
#unleashed // #40forward

5. • That we’re a group because we
showed up
!
• That we’re going to be real and do
hard things
!
• That we don’t gossip
!
• That we can build confidence
doing everyday things
!
• That it’s okay to draw inspiration
from others and match or mimic
what they do
!
• That you start anytime (like now)

6. Who’s willing to tell a story from
the confidence assignment?
KATE O’REILLY // @CLEVERKATE
#unleashed // #40forward

7. Six things you can do to gain confidence today:
!
!
• Get enough sleep. Sleep solves ALL THE PROBLEMS.
!
• Eliminate jealousy as an emotion. Want something for yourself? Go
get it.
!
• Wear only clothes (AND SHOES) that make you feel amazing. Protip:
If someone says you look great in a color: believe them and wear it
more.
!
• Break up with one person that weighs you down. Actively/or fade
away. Be kind and be done.
!
• Go to a restaurant and order the first thing that looks good. Then
put the menu down and talk to the person across from you about
real things.
!

8. BUILDING BLOCKS OF
CONFIDENCE
!
!
!
ACCEPTANCE
VALUES RISK
COMMUNITY

10. Risk is all about being
uncomfy with
something and then
deciding to do it anyway.
KATE O’REILLY // @CLEVERKATE
#unleashed // #40forward

11. So, how do we overcome our
tendency to play it safe to identify
which risks are worth taking?
!
!
!
Start by identifying something (uncomfy or potentially risky) you
have going on in your life right now and then doing the following
exercise.

12. 1) What does being more courageous look like? How does it feel?
2) How will inaction look one year from now?
3) Is my fear of failure causing me to overestimate the size of the
risk, underestimate myself, and/or is it holding me back?
KATE O’REILLY // @CLEVERKATE
#unleashed // #40forward

13. Whatever answers come into
your mind, take notice!
!
!
!
!
You are wired to both overestimate the size of risks and to
underestimate your ability to handle them.

14. By acknowledging our
fears, we tame them.
Wait, what?

15. Five* ways to take a risk
and increase confidence
that you can do right away.
!
!
!
!
!
*Choose one or two. All five at once might make you dislike me intensely.

16. • Try a new physical activity.
!
• Update your resume and submit for a
job you think is out of your league.
!
• Ask for what you really want once
this week, twice next, and so on.
!
• Take an improv class.
!
• Put holes in walls. (Or a color on it.)

17. I’m not telling you it’s going
to be easy.
I’m telling you it’s going to be
worth it.

18. Thank you.
Call and write often.
@cleverkate // kate@clever-kate.com