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Do Work You Love “Manage Your Risk”
aka “Make a Good Plan”
Q1. Where are you guys at?
Q2. What outcomes do we want?
Q2. What outcomes do we want?
Freedom and Purpose.
Q3. How are you finding this?
Q3. How are you finding this?
Exciting?
Q3. How are you finding this?
Exciting? Frustrating?
Q4. Who still doesn’t know what
they want to do?
What separates the people who dream but let the blockers and the risk and the fear stop them?
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?
1. THEY SHELVE-ALL-OR-NOTHING THINKING
1. THEY SHELVE-ALL-OR-NOTHING THINKING
Full-Time Job vs No Job At All
1. THEY SHELVE-ALL-OR-NOTHING THINKING
Awesome Salary vs No Salary At All
1. THEY SHELVE-ALL-OR-NOTHING THINKING
Nirvana Fulfillment vs Wrong Move
1. THEY SHELVE-ALL-OR-NOTHING THINKING
They find the way that works based on what they say they
want in their lives.
2. THEY HAVE A CLEAR COMPASS
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)
2. THEY HAVE A CLEAR COMPASS
They are happy to exclude options based on their values, principles and
personal requirements.
3. THEY RELAX ABOUT THE OUTCOME
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.
3. THEY RELAX ABOUT THE OUTCOME
And they do / act / experiment their way towards things that interest them. Whilst managing their risk.
4. THEY ACT (NOT THINK) THEIR WAY FORWARDS
Even when they don’t know what they are acting towards.
4. THEY ACT (NOT THINK) THEIR WAY FORWARDS
Through doing this they create new opportunities they couldn’t
have seen when they were thinking
4. THEY ACT (NOT THINK) THEIR WAY FORWARDS
5. THEY USE THEIR FEARS
They turn blockers into actions.
5. THEY USE THEIR FEARS
They turn risks into decision criteria (i.e. I need this
amount of financial security)
5. THEY USE THEIR FEARS
And they use risks to make good plans.
5. THEY USE THEIR FEARS
Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING
Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING
1. EVERYTHING IS AN EXTREME PREDICTION
Escapees Stuck People 1. SHELVE-ALL-OR-NOTHING THINKING
1. EVERYTHING IS AN EXTREME PREDICTION
2. HAVE A CLEAR COMPASS
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
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
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
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
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
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
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
@escroberto
My story
My story This talk
@escroberto
I’m not here to sell you on risk!
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.
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.
And we should use our fears
And we should use our fears
Underneath layers of all-or-nothing thinking are genuine concerns that need to
be managed.
“Manage your risk” is simply another term for “Make a good plan”.
“Manage your risk” is simply another term for “Make a good plan”.
And the definition of “A Good Plan” is entirely up to you.
“But I still don’t know what I want”
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”
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
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
Thoughts on dreaming big
Thoughts on dreaming big and CATASTROPHISING!
Thoughts on dreaming big and CATASTROPHISING!
Thoughts on getting real
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.
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
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
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
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
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.
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
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)
Good entrepreneurs aren’t good risk takers. They’re good risk
managers. Same goes for career changers or freelancers.
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
The sabbatical option
The sabbatical option
- 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
The rapid retrain
The rapid retrain
The working holiday Maeve – Occupational therapist
Ben – Media & technology consultant
Maeve – Occupational therapist Ben – Media & technology
consultant
The working holiday
The paid programme
The paid programme
The new job
The new job
The shed option
The shed option
The contracting option
The contracting option
The fake plan plan
The fake plan plan
The fake plan plan
The fake plan plan
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
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
Unhelful thinking/behaviour 1. Spending our way through misery (or go travelling to figure it out)
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)
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
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
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)
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)
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
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)
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
The heart of this risk thing…
THE MONEY QUESTION!
“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
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
“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
Your escape is like a startup “A startup is an organisation
formed to search for a repeatable and scalable business model” –
Steve Blank
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)
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
Story: Dom Jackman Three-Account Saving System: Account A: Fixed Costs Account B: Monthly Budget Account C: Salary/Income
Chapter 5 – The Escape Manifesto
Strategies for the money question • Save as much money as possible
• Spend less, pay down debt • Invest in assets, avoid liabilities
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
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
Paul Smith on Purity
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
We are bad at risk
And we expect the worst
Worrying is praying for what you don’t want.
Risk Danger
Worry Fear
Risk Danger
Worry Fear a situation involving exposure to danger.
the possibility of suffering harm or injury.
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.
Risk Danger
Worry Fear
&
&
ARE BROADLY REAL - THEY NEED TO BE MANAGED
Risk Danger
Worry Fear ARE BROADLY REAL - THEY NEED TO BE MANAGED
ARE BROADLY IMAGINARY – DON’T LET THEM STOP YOU
&
&
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
Leah Woodward
Leah Woodward
In 5 sentences The obituary you want
Regret Avoidance - exercise
In 5 sentences The obituary you are heading for
Regret Avoidance - exercise
Between the two you have A) a decision to make about your life and B) a prompt to make a good plan
HOMEWORK
The Escape Mindset 1. Escaping is not a moment, it’s a process
The Escape Mindset 1. Escaping is not a moment, it’s a process 2. It’s not even a process, it’s a mindset
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
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
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
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
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
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…
- THANK YOU -
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!)