February 18, 2019

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I’m a planner at heart. It’s something I’ve always done, naturally, ever since childhood. I planned out my entire college course progression before I even started college—but that kind of planning isn’t what I want to talk about today. I want to discuss why you should plan for the worst… Before the worst happens.

That sounds depressing, doesn’t it?

But those who plan for the worst are the ones who make it out alive.

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

Wait, what?

Hold up, Colleen, what are you even talking about? “Make it out alive”?


At my job, I’m on our Safety Committee. It sounds like the “safety police” until you understand that my company’s #1 core value is, in fact, safety, and we just had a Safety Conference. It’s a big deal.

And safety is something that needs to carry over to our personal lives.

The best way to be safe is to plan. Prepare. Understand what the stakes are and to know what you’re going to do if the worst happens.

Ergo, plan for the worst before it strikes.

Fear Setting

Tim Ferriss actually mirrors this with his Fear Setting exercise.

He makes a list of the worst possible things that could happen for whatever he’s fearing, and then he writes down what he would do if the worst happens, and what the best possible outcome is.

For example, if my worst fear is losing my job, then the worst that could happen is that I also lose my health insurance and can’t afford my diabetes supplies.

Whew. Yeah, that’s actually my worst fear. It’s bad. Insulin is approximately 1700% more expensive than it was when I was first diagnosed.


That’s the worst that could happen.

But what’s the best possible outcome of losing my job? I have the free time and energy to pour into the side hustles that I’ve cultivated over the past year. While insurance on the marketplace exchange is pretty trash, it’s something.

Full disclosure: I know that this fear is irrational. I love my job, and they love me. But I’m paranoid and having multiple streams of income helps alleviate that paranoia.

Safety Question Time!

How many of you walked the emergency exit route at the last hotel you stayed in?


How many of you have informed the front desk about security or safety concerns during your stays?

(More crickets)

And… How many of you have actually had to evacuate a hotel at 3 in the morning when a fire alarm went off—whether there was a fire or not?

(Small noises of “maybe”)

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

This is a simple example.

And it’s 100% related to not only your physical health but your mental health as well.

Can you imagine waking up from the dead of sleep to a blaring fire alarm and having to stumble your way into the hall, realizing you have no idea how to get out?

Panic sets in.

Where are the exits? Where’s the fire?

The last thing on your mind is your shoes, your clothing, or your car keys and phone.

But those are the things you’ll need most when you actually make it outside.

The great thing about planning for the worst is that you can do it for all types of situations, not just a hotel fire at 3 AM. To get started, you just need to ask yourself—and honestly answer—a few questions.

What Are The Hazards?

For an early-morning hotel fire, it’s obviously the fire and the risk that you won’t be able to get out.

But for other situations or fears, you might have to do some deeper thinking.

Let’s use my worst fear as an example: losing my job.

The hazards include:

  1. Losing my health insurance, which introduces these hazards:
    1. Rationing insulin
    2. Losing coverage for my insulin pump and continuous glucose monitor
    3. A decline in health—and an increase in A1c values ← this is the measure of how well I’m controlling my diabetes, so it’s an important number to keep low.
    4. Open-market insurance too expensive to cover with a “pre-existing condition”.
  2. Loss of stable income could mean…
    1. Being unable to afford rent
    2. Going into credit card debt to pay the bills
    3. Needing to switch diets to save money on groceries—low carb can be expensive
    4. Having to move back in with my parents or in-laws
  3. Suffering depression and anxiety, including…
    1. Feeling worthless and justified in my imposter syndrome
    2. Not feeling like doing anything productive
  4. Letting commitments lapse, which could lead to…
    1. The collapse of social reputation
    2. Loss of side-hustle clients—loss of side-income

Think of this as a mind-mapping exercise. Try to dig down really deep to find all the associated hazards and potential outcomes related to those hazards.

How Can You Mitigate Those Hazards?

What can you—or I—do right now to stop these hazardous outcomes in their tracks? For the hotel fire, the best solution is to walk the emergency exits. Make sure you know which direction you turn when leaving your room, about how long you walk to reach the door, and how many flights of stairs down you need to go.

Also, it’s a good idea to make sure you can grab your essentials before leaving the room—and that you’re wearing your shoes.

For my hypothetical hazardous situation, let’s walk through mitigation.

The first and most easily implemented mitigation is to build a robust emergency fund.

This is one of my 2019 goals—to fully-fund a six-month living expenses fund that would cover all true expenses and bills for at least six months following a job loss.

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

Health Insurance

The number we’ve calculated, though, does not include open-market health insurance. It probably should, but during my unemployment in 2017 I was covered by my dad’s insurance so I didn’t consider budgeting for it. That’s dropping off this year, and I’m a lot sad about it.

Now that I’m writing this, it’s probably a really good idea to price out what open-market insurance would cost per month and factor that into our emergency fund.

Insulin Rationing

This is a real problem for people who can’t afford their medications. I have never had to ration insulin, thank God, and I hope I never will.

But mitigating this awful hazard includes things like stocking up on insulin while I can and ensuring my diet is consistently low-carb so I don’t experience any wild blood sugar swings that would cause me to use more insulin than usual.

Pump/CGM Coverage

Similar to insulin, I should stock up on pump and CGM supplies. this is more difficult to do because suppliers ship on a 3-month schedule and generally don’t let you order more in advance. But if I can squeeze an extra day out of an infusion set every once in a while, or successfully restart a CGM session, then I can extend the life of my supplies.

Decline in Health

Mitigating a decline in health is obviously done by maintaining my health. I know I feel like crap if I eat too much, or if I eat carbs because doing both will increase my blood sugar—which means I need to take more insulin.

It’s a weird loop of interconnectedness.

The best thing to do right now is to maintain or improve my health so that I’m less likely to experience a decline in it.

Exchange Insurance Too Expensive

Like mentioned above, mitigate this by working the cost into my emergency fund.

Loss of Stable Income

Let’s be honest. Everything in this section can be somewhat addressed by saving a sufficient emergency fund.


You generally can’t get an apartment if you can’t prove income equal or greater to three times the rent. If you’re currently living someplace expensive AF when you lose your job, it’s going to be super tough to move.

Build rent into your E-Fund.

Credit Card Debt

I’ve only carried a balance ONCE in my life on any of my credit cards, and will never do so again. I got hit by a fee and an increase in my APR literally the day after the due date, despite making a payment for over the minimum.

Credit cards are no joke, you guys. And credit card debt is scary as hell.

My heart goes out to all of you who are living under that black cloud.

If I did end up losing my job, I would immediately cease any plans to open new credit cards and focus on keeping my balances low. That means no travel-hacking because if you’re living off your E-Fund you won’t be spending anything on travel anyway.

I actually pay all our cards every Friday because I’m paranoid.

Build the cost of things into your E-Fund so that you don’t carry credit card debt.

Expensive Groceries

Despite how cheap the “staples” are, I would be loath to go back on a carby diet because it would seriously mess with my health.

For this one, I would specifically make sure I can afford my low-carb essentials with E-Fund money.

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

Living With Parents or In-Laws

We did this after my 2017 job loss.

It was not bad, but it wasn’t great, either. We lived with them for six months, bless their hearts, but I was sooooo excited to get out and make our own space again after I landed my full-time job.

If we did end up having to move back in with either set of our parents, We’d probably do a lot to reduce our belongings first. We were able to fit all our stuff into 80 square feet in their garage, but it was a super-tight fit and that was after getting rid of a few things before we actually moved in—like the desk I’d had since childhood.

This is related to rent—make sure you build it into your E-Fund.

Depression & Anxiety

Going to therapy while it’s still covered by insurance is a good strategy. I did this leading up to the end of my job in 2017, and it helped so much with working through the horrible feelings and thoughts I had about it. 

Being unemployed sucks—it sucks bad, especially when you don’t have a back-up plan or a side business to grow. 

Depression and anxiety are quick to move in, quick to take over thought processes, and quick to sabotage any good feelings. The advice to “stay positive” can fall flat on people with depression and anxiety following a job loss. 

I know, because it did for me. It didn’t feel like the people “encouraging” me really understood what was going on or how I really felt about it. People tried to give advice about searching for a job—some of that advice was over 30 years out-of-date or relevant to positions that did not match my career level or skill set.

But it’s hard to fully mitigate depression and anxiety. If you’ve suffered from them in the past you know how easy it is to slip back into those feelings. They’re like a blanket. A victim blanket.

Feeling Worthless and Justified in My Imposter Syndrome

Imposter syndrome just means that you feel like a fake in what you do, despite any current or past success and praise for it. It’s the feeling of waiting for the other shoe to drop—for your boss to realize you actually suck at your job. 

And if you lose your job—you’re primed to believe that you actually can’t do what you said you could—or what you actually did for whatever length of time you did it.

It’s hard to mitigate this one.

Really hard.

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

It’s probably best to just be aware that this can occur. Being able to recognize the spiral of imposter syndrome and worthlessness is invaluable to getting yourself out of it, or getting help.

A good idea, though, is to build up a repository of the praise you’ve received, the things you’ve accomplished, and the proof that you’re not a fraud.

If you ever feel the claws of imposter syndrome you can pop open that repository and bask in all the awesome praise you’ve received.

Lack of Motivation to Be Productive

Lack of motivation comes from a lot of places, and motivation is fleeting regardless of the state of your employment. The only real way to combat this is to build habits and your willpower muscle to take the place of motivation.

Make it automatic—you don’t want to have to think about doing things that keep you productive.

Lapse of Commitments

I take my commitments seriously, as everyone should. I feel sick to my stomach if I’m in danger of breaking a commitment to someone—and myself. As Gretchen Rubin would say, out of the Four Tendencies, I’m an Upholder.

Understandably, people can fall to the point of apathy regarding commitments, especially during joblessness. A good way to combat this is to again, utilize therapy while it’s covered by insurance (or you can afford it) to work through those fears.

Even having someone check in on you—an accountability partner—can help keep those thoughts at the front of your mind and less likely to let them fall through the cracks.

A Collapse of Social Reputation

If you do end up letting those commitments slide, your social reputation can go down the drain.

This is sad. 

Don’t your friends understand that it’s hard to be unemployed? That apathy and depression and anxiety are all expected? 

Well, sure. They should. But you should also understand that humans are social animals. If we lose our social interactions by the loss of reputation, it’s going to feel much worse.

Possible ways to mitigate:

  • Be open and honest about your struggles—not on social media, but with a few close friends you can rely on.
  • Ask for an accountability partner to check in on you weekly (or daily, if you need it).
  • Make a concerted effort to spend time with your friends—but only the ones who build you up. There’s no benefit in hanging around toxic people.

Loss of Clients/Side-Hustle Income

What if you have a side-business? If you lose your full-time job and end up feeling too depressed to do anything about your side-business, you risk losing your clients—and all that extra money that could be helping you out.

What to do about this?

Don’t just build up your client-base, also look into creating passive streams of income. Things like eBooks, digital products, affiliate promotions, and online courses you can sell to either your email list (if you’re a blogger/have a website) or another audience you have.

Utilize the knowledge in any of the online courses you’ve taken. What could you implement from those to boost your passive income?

If you have the dollars to invest (before the worst happens), what programs could you invest in that would give you the best return? 

I am biased here—online courses are one of my biggest investments. Since 2017, I’ve invested over $2000 in online courses—some of which I haven’t even opened yet because I have so many to choose from.

As time goes by I’m slowly earning that investment back, and fully expect to do so this year alone.

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

Flip the Script: What’s the Best That Could Happen?

Now that we’ve defined the hazards and brainstormed ways to mitigate them, let’s tackle your mindset.

If you experienced the worst that could happen, what is the best possible outcome that could occur?

For the hotel fire, the best possible outcome is that you and all your belongings make it out alive.

That’s pretty straightforward.

But for things like job loss, it’s less so. 

Considering I’ve been building my side-hustle for over a year, now, and have actually made money from it, I have proven to myself that it can be done. 

If I lost my full-time job and properly prepared for it, what’s the best possible result?

  • I have more time to pour into my side-hustles—which would then become my full-time hustles.
  • More time and energy spent on those things means increasing the income from them. 
  • I would have more time to go through the courses I’ve purchased and take action on them.
  • I could scale my business and end up making more than I currently make at my full-time job.

Isn’t that mind-blowing? 

It’s also scary! Scary that I could ever achieve that kind of success with a side-hustle. But it’s 100% achievable. Thousands of people have turned their side-hustles into full-time jobs. They’ve even quit full-time jobs to expand their side-businesses. 

Proof that other people have done it is proof that you can do it too—but only if you take action, develop a plan, and roll with the punches.

Have you considered what you would do if the worst happens? No? It's important to plan for the worst so that you're not left scrambling -- in any situation.

The Worst is Not Guaranteed

Possibly the best thing you’ve read this whole article—is that the worst thing you can think of is not guaranteed to occur.

You may spend your entire life without ever experiencing a hotel fire.

I hope that’s true.

You may spend your entire life never dealing with a job loss. This is less likely, but there are people who have stayed with one company their entire career. My dad has been at his company for over 30 years. It’s more common among the older generations.

Your greatest fears may never come to pass. 

[bctt tweet=”Your greatest fears may never come to pass, but if they do… Don’t you want to have a plan in place to deal with it?” username=”inspiredforward”]

But the exercise of preparing for them—planning for them—making sure you know what you should do to mitigate the damage—that is invaluable

It keeps you from panicking and drowning in the chaos of those situations.

It makes sure you know what to do and when to do it, and what to expect.

Only you know your worst fears. 

So what are you waiting for? Start planning for them.

Has your worst fear come true? How did you react? What would you do differently now if you had time to plan for the worst to happen again? Join the discussion below!

About the author 


Life coach, author, engineer, and host of the podcast This is Type 1: Real Life with Type 1 Diabetes. I teach T1Ds how to feel better without changing how they manage it.

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  1. This is something we have always done. From food storage, water storage, first aid kits, 72 hour kits, car safety, financial planning. Yep we plan.

  2. Lol! I love this because I can totally relate! I think it’s why I love to read dystopian books and watch disaster movies, so I can plan out escape and survival plans in my head. These are terrific suggestions!

  3. Wow great ideas! To be honest you really got me thinking about that emergency fund. Thank you. And I’m such a believer in side hustles and hoping mine will soon become my only hustle!

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