part 4: manage your risk

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Do Work You Love “Manage Your Risk” aka “Make a Good Plan”

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Page 1: Part 4: Manage Your Risk

Do Work You Love “Manage Your Risk”

aka “Make a Good Plan”

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Q1. Where are you guys at?

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Q2. What outcomes do we want?

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Q2. What outcomes do we want?

Freedom and Purpose.

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Q3. How are you finding this?

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Q3. How are you finding this?

Exciting?

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Q3. How are you finding this?

Exciting? Frustrating?

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Q4. Who still doesn’t know what

they want to do?

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What separates the people who dream but let the blockers and the risk and the fear stop them?

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What separates the people who dream but let the blockers and the risk and the fear stop them?

From those who ACT on their dreams and make big transitions?

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1. THEY SHELVE-ALL-OR-NOTHING THINKING

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1. THEY SHELVE-ALL-OR-NOTHING THINKING

Full-Time Job vs No Job At All

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1. THEY SHELVE-ALL-OR-NOTHING THINKING

Awesome Salary vs No Salary At All

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1. THEY SHELVE-ALL-OR-NOTHING THINKING

Nirvana Fulfillment vs Wrong Move

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1. THEY SHELVE-ALL-OR-NOTHING THINKING

They find the way that works based on what they say they

want in their lives.

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2. THEY HAVE A CLEAR COMPASS

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2. THEY HAVE A CLEAR COMPASS

They get clear on their motivations and the ingredients of what they

are aiming at (if not the specifics)

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2. THEY HAVE A CLEAR COMPASS

They are happy to exclude options based on their values, principles and

personal requirements.

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3. THEY RELAX ABOUT THE OUTCOME

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3. THEY RELAX ABOUT THE OUTCOME

They don’t get hung up on the specific details of what exactly they

want to end up doing.

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3. THEY RELAX ABOUT THE OUTCOME

And they do / act / experiment their way towards things that interest them. Whilst managing their risk.

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4. THEY ACT (NOT THINK) THEIR WAY FORWARDS

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Even when they don’t know what they are acting towards.

4. THEY ACT (NOT THINK) THEIR WAY FORWARDS

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Through doing this they create new opportunities they couldn’t

have seen when they were thinking

4. THEY ACT (NOT THINK) THEIR WAY FORWARDS

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5. THEY USE THEIR FEARS

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They turn blockers into actions.

5. THEY USE THEIR FEARS

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They turn risks into decision criteria (i.e. I need this

amount of financial security)

5. THEY USE THEIR FEARS

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And they use risks to make good plans.

5. THEY USE THEIR FEARS

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Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

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Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

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Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

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Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

Page 33: Part 4: Manage Your Risk

Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

3. RELAX ABOUT THE OUTCOME & START

Page 34: Part 4: Manage Your Risk

Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

3. RELAX ABOUT THE OUTCOME & START

3. NEED TO KNOW BEFORE THEY START

Page 35: Part 4: Manage Your Risk

Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

3. RELAX ABOUT THE OUTCOME & START

3. NEED TO KNOW BEFORE THEY START

4. ACT (NOT THINK) THEIR WAY FORWARDS

Page 36: Part 4: Manage Your Risk

Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

3. RELAX ABOUT THE OUTCOME & START

3. NEED TO KNOW BEFORE THEY START

4. ACT (NOT THINK) THEIR WAY FORWARDS

4. THINK (NOT ACT) THEIR WAY FORWARDS

Page 37: Part 4: Manage Your Risk

Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

3. RELAX ABOUT THE OUTCOME & START

3. NEED TO KNOW BEFORE THEY START

4. ACT (NOT THINK) THEIR WAY FORWARDS

4. THINK (NOT ACT) THEIR WAY FORWARDS

5. USE THEIR FEARS TO GUIDE DECISIONS

Page 38: Part 4: Manage Your Risk

Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING

1. EVERYTHING IS AN EXTREME PREDICTION

2. HAVE A CLEAR COMPASS

2. AREN’T CLEAR ON THEIR INGREDIENTS

3. RELAX ABOUT THE OUTCOME & START

3. NEED TO KNOW BEFORE THEY START

4. ACT (NOT THINK) THEIR WAY FORWARDS

4. THINK (NOT ACT) THEIR WAY FORWARDS

5. USE THEIR FEARS TO GUIDE DECISIONS

5. ALLOW THEIR FEARS TO STOP THEM

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@escroberto

My story

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My story This talk

@escroberto

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I’m not here to sell you on risk!

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I’m not here to sell you on risk!

None of us would be here if changing career and trying to build a life of meaning was easy.

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I’m not here to sell you on risk!

None of us would be here if changing career and trying to build a life of meaning was easy. But it doesn’t have to be as gung-ho as we

imagine it will be when we’re lying in bed at 3 am.

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And we should use our fears

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And we should use our fears

Underneath layers of all-or-nothing thinking are genuine concerns that need to

be managed.

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“Manage your risk” is simply another term for “Make a good plan”.

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“Manage your risk” is simply another term for “Make a good plan”.

And the definition of “A Good Plan” is entirely up to you.

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“But I still don’t know what I want”

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AWESOME. So you need an action plan for getting to a

place where you can figure out what you want!

“But I still don’t know what I want”

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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Thoughts on dreaming big

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Thoughts on dreaming big and CATASTROPHISING!

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Thoughts on dreaming big and CATASTROPHISING!

Thoughts on getting real

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When we move a fear from general to specific we can

manage it – it is when we are predicting overall disaster that it is completely unmanageable.

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The Escape Landscape Same job different company

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

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The Escape Landscape Same job different company

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

Employment

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The Escape Landscape Same job different company

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

This is pretty easy?

Employment

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The Escape Landscape Same job different company

Employment

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

This is pretty easy?

Entrepreneurship

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The Escape Landscape Same job different company

Employment

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

This is pretty easy?

Entrepreneurship

This is harder and is what we need help with.

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The Escape Landscape Same job different company

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

Difficulty

Risk

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The Escape Landscape Same job different company

Same job different country

Same job different industry

New job / industry / country

Freelance Portfolio Career

One-Person Business

Start Growth Business

Difficulty

Risk (and fear) (and worry)

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Good entrepreneurs aren’t good risk takers. They’re good risk

managers. Same goes for career changers or freelancers.

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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The sabbatical option

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The sabbatical option

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- The idea - The 4-day week The 3-day week The 2-day week

- The paying customers - The contract gig

- The investment - The full escape

The staggered escape

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The rapid retrain

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The rapid retrain

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The working holiday Maeve – Occupational therapist

Ben – Media & technology consultant

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Maeve – Occupational therapist Ben – Media & technology

consultant

The working holiday

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The paid programme

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The paid programme

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The new job

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The new job

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The shed option

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The shed option

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The contracting option

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The contracting option

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The fake plan plan

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The fake plan plan

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The fake plan plan

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The fake plan plan

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Maybe you shouldn’t have a plan... Five reasons you shouldn’t have a cushion before you quit: 1.  Lights a fire under your ass 2.  Forced to get creative 3.  Learn to focus 4.  Constraints drive action 5.  The sooner you start, the

sooner you can succeed

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out)

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants)

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants) 3.  Comparing ourselves to others, not defining success for ourselves

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants) 3.  Comparing ourselves to others, not defining success for ourselves 4.  Taking 1, 2, 3 years out for post-grad study

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants) 3.  Comparing ourselves to others, not defining success for ourselves 4.  Taking 1, 2, 3 years out for post-grad study 5.  Not investing in ourselves (new skills, new experiences)

Page 92: Part 4: Manage Your Risk

Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants) 3.  Comparing ourselves to others, not defining success for ourselves 4.  Taking 1, 2, 3 years out for post-grad study 5.  Not investing in ourselves (new skills, new experiences) 6.  Thinking through new options, rather than doing (mini-tests)

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants) 3.  Comparing ourselves to others, not defining success for ourselves 4.  Taking 1, 2, 3 years out for post-grad study 5.  Not investing in ourselves (new skills, new experiences) 6.  Thinking through new options, rather than doing (mini-tests) 7.  Thinking in all-or-nothing terms at the expense of viable options

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Unhelful thinking/behaviour 1.  Spending our way through misery (or go travelling to figure it out) 2.  Allowing our current lifestyle to own us (needs becoming wants) 3.  Comparing ourselves to others, not defining success for ourselves 4.  Taking 1, 2, 3 years out for post-grad study 5.  Not investing in ourselves (new skills, new experiences) 6.  Thinking through new options, rather than doing (mini-tests) 7.  Thinking in all-or-nothing terms at the expense of viable options 8.  Not asking (for a change, for flexible work, for a sabbatical)

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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The heart of this risk thing…

THE MONEY QUESTION!

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“To state the obvious, personal finance is personal. Just as you shouldn’t let anyone else determine your goals and values, you should also seek to maintain control over your own financial priorities. More than almost any other aspect of your identity, if you don’t have clarity of purpose over how you view the role of money in your life, you’ll likely end up going along with what other people do.” Chris Guillebeau The Art of Non-Conformity

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Let your fears guide you: Fears are not all bad! They can be a great way to ensure that your plan covers what it needs to. If you have a nagging fear about something that is not covered in your current plan, it is a good indication that you need to address it. -  How will I pay for a medical emergency? -  How will I replace paid time off? -  How much am I going to pay in taxes? -  What if my clients don’t pay on time?

Pamela Slim Escape from Cubicle Nation

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“How many times have you opened your bills, winced, then shrugged and said, ‘I guess I spent that much’?” Ramit Sethi, I Will Teach You To Be Rich

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Your escape is like a startup “A startup is an organisation

formed to search for a repeatable and scalable business model” –

Steve Blank

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HOMEWORK: What is Your Runway?

A.  Minimum you can live on per month (during your escape) B.  How many months you think you’ll need to figure it out C.  Ideal recurring income after the transition (post-escape) D.  Your total escape fund (pre-escape savings)

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HOMEWORK: What is Your Runway?

A.  Minimum you can live on per month (during your escape)

B.  How many months you think you’ll need to figure it out

C.  Ideal recurring income after the transition (post-escape)

D.  Your total escape fund (pre-escape savings)

A.  £4000

B.  12 months

C.  £60,000 per annum

D.  4000 x 12 = £48,000

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Story: Dom Jackman Three-Account Saving System: Account A: Fixed Costs Account B: Monthly Budget Account C: Salary/Income

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Chapter 5 – The Escape Manifesto

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Strategies for the money question •  Save as much money as possible

•  Spend less, pay down debt •  Invest in assets, avoid liabilities

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Strategies for the money question •  Save as much money as possible

•  Spend less, pay down debt •  Invest in assets, avoid liabilities

•  Keep a salary for as long as possible •  Full-time – your job •  Part-time – your job •  Contracting

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Strategies for the money question •  Save as much money as possible

•  Spend less, pay down debt •  Invest in assets, avoid liabilities

•  Keep a salary for as long as possible •  Full-time – your job •  Part-time – your job •  Contracting

•  Have your eyes open during the gap •  Make and stick to a budget (be conservative) •  Find ways to cover costs during this period

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Paul Smith on Purity

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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We are bad at risk

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And we expect the worst

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Worrying is praying for what you don’t want.

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Risk Danger

Worry Fear

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Risk Danger

Worry Fear a situation involving exposure to danger.

the possibility of suffering harm or injury.

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Risk Danger

Worry Fear a situation involving exposure to danger.

the possibility of suffering harm or injury.

the state of being anxious and troubled over actual or potential problems.

an unpleasant emotion caused by the threat of danger, pain, or harm.

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Risk Danger

Worry Fear

&

&

ARE BROADLY REAL - THEY NEED TO BE MANAGED

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Risk Danger

Worry Fear ARE BROADLY REAL - THEY NEED TO BE MANAGED

ARE BROADLY IMAGINARY – DON’T LET THEM STOP YOU

&

&

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Today’s Menu 1. Let’s define “Escaping”

2. Strategies for the transition

3. Identify unhelpful behaviour

4. Get close to the numbers

5. Distinguish risk vs worry 6. Practice regret avoidance

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Leah Woodward

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Leah Woodward

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In 5 sentences The obituary you want

Regret Avoidance - exercise

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In 5 sentences The obituary you are heading for

Regret Avoidance - exercise

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Between the two you have A) a decision to make about your life and B) a prompt to make a good plan

HOMEWORK

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The Escape Mindset 1.  Escaping is not a moment, it’s a process

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset 3.  It’s simply a decision to not settle, even if it takes years

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset 3.  It’s simply a decision to not settle, even if it takes years 4.  It’s simply a decision to make smart, personal decisions

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset 3.  It’s simply a decision to not settle, even if it takes years 4.  It’s simply a decision to make smart, personal decisions 5.  And that starts by making a good plan & managing risk

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset 3.  It’s simply a decision to not settle, even if it takes years 4.  It’s simply a decision to make smart, personal decisions 5.  And that starts by making a good plan & managing risk 6.  Even if the plan is to take steps to find the right plan

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset 3.  It’s simply a decision to not settle, even if it takes years 4.  It’s simply a decision to make smart, personal decisions 5.  And that starts by making a good plan & managing risk 6.  Even if the plan is to take steps to find the right plan 7.  Living a life on your own terms is a fight – it takes everything

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The Escape Mindset 1.  Escaping is not a moment, it’s a process 2.  It’s not even a process, it’s a mindset 3.  It’s simply a decision to not settle, even if it takes years 4.  It’s simply a decision to make smart, personal decisions 5.  And that starts by making a good plan & managing risk 6.  Even if the plan is to take steps to find the right plan 7.  Living a life on your own terms is a fight – it takes everything 8.  But we all know what the alternative is…

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- THANK YOU -

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Further reading 1.  I Will Teach You To Be Rich (Ramit Sethi) 2.  Stoicism 101: A Pratical Guide for Entrepreneurs

(Tim Ferriss’s blog) 3.  Your Money or Your Life (Joseph R. Dominguez) 4.  Rich Dad, Poor Dad (Robert Kiyosaki) 5.  Escape from Cubicle Nation (Pamela Slim) 6.  The Art of Non-Conformity (Chris Guillebeau) 7.  The Escape Manifesto (by me!)

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