How to Plan to Fail (And Why You Should)

A planner with colorful accessories including washi tape, book bands, and planner tabs.

If you want to achieve success, then you need to plan to fail.

It’s easy to do well when everything is going smoothly. Your project is hitting all its targets. You have all the time and energy for your goals. You have an ample budget for your business. But what do you do when things suddenly go off course? How do you respond when challenges arise? 

It may sound counter-intuitive but planning for failure is key to staying on track. 

Why you succeed when you plan to fail

Now you might be thinking: Why should I plan to fail? Isn’t that pessimistic? Or counter-productive?

Worrying about failure won’t get you very far. But preparing for various scenarios and shoring up your resources will help you respond effectively to the unexpected. Planning to fail isn’t about giving yourself unnecessary stress and anxiety. It is looking at the long-term view and being realistic about the obstacles you might encounter along the way. 

No one likes dealing with surprises that come out of left field. But a solid contingency plan can help you re-stabilize and bounce back.

How to create a backup plan

When devising your back up plan, you’ll want to consider all the different variables that could throw you for a loop. Potential curveballs can include: a reduced budget, a changing deadline, surprise expenses, cancellations, health issues, and more. 

When doing this exercise, ask yourself:

  • What are the different roadblocks that I may run into?
  • What are the worst case scenarios? For example, if you’re producing a high-level event, the worst scenario could be the guest speaker cancels at the last minute. 
  • What are things I can do to prevent the worst case scenario from happening? To use the high-level event example, you check-in with the guest speaker one month and one week out. You can have the guest speaker sign a contract.
  • What actions can I take if a worst case scenario unfolds? So if your guest speaker cancels at the last minute, have back-up speakers you can reach out to or book a speaker you’ve had in the past.

Here are some of the different ways that you can create backup systems for your work and life. 

Build up a network at work

Strengthen your resources by building a strong network at the office.

Whether it’s to get advice during a work emergency, or have a back-up arrangement for when you’re out sick, a solid network at the office can make your life so much easier. And with 80 percent of new career opportunities coming through personal connections, it pays to strengthen your network. 

How to build a strong network at the office:

  • Work with people outside of your team. It’s so easy to stay within our group at the office, but make it a point to collaborate with people outside of your team. Maybe it’s working on an interdepartmental project or sharing knowledge and resources. In doing so, more people will know your name and your work. 
  • Have coffee with one new person a month. Maybe it’s a colleague you admire or a dream client you’d love to work with, challenge yourself to meet with at least one new person a month. This is especially helpful if you’re a freelancer or small business owner and don’t have an in-house network to rely on. And don’t forget to help out your contact and make meaningful contributions. A strong professional relationship is mutually beneficial and harmonious. 

Have a rainy day plan for your goals 

Maybe your new year’s resolution is to exercise more or finally get started on writing your novel. Ensure the success of your goals by planning for obstacles

For example, a rainy day can be an obstacle for your fitness goal. Or feeling tired and unmotivated can be an obstacle for your writing goal. . 

Identify your obstacles and “rainy days” and have a backup plan for them. You can still work on your goal without missing a beat. 

How to create a rainy day plan:

  • Reduce your target. If feeling tired is your obstacle, then lower your target. Instead of running for thirty minutes, aim for ten. Instead of writing 1,000 words a day, aim for 200. Set your target low and you’ll have an easier time going through with it. 
  • Find a different environment. If it’s raining outside, do an online workout. If you can’t work in your home, try writing in a coffee shop. Switching up your environment can help you follow through with your goal with minimal disruption. 

Create a financial safety net

No one likes to think about the possibility of getting laid off or losing a big client. But emergencies happen and circumstances can change. To help you mitigate financial emergencies, start building a financial safety net now. 

How to create a financial safety net:

  • Create an additional income stream. Whether it’s taking on freelance assignments or doing part-time work, an additional income stream will help you create a financial buffer in case of an emergency. 
  • See where you can cut costs. When it comes to saving money, don’t fixate on the small expenses like a glass of wine at happy hour. Focus on your money dials instead. Money dials are your financial priorities. As Ramit Sethi writes: “They’re called Money Dials because you can “tune” them up or down — just like a dial.” 

So if you want to buy a glass of wine then buy it. But if you’re okay with spending less money on new clothes every month, then cut back. This helps you be realistic about your spending and connect your money with your priorities. 

Other ideas for a backup plan:

  • Backup your files. Prevent any future headaches by saving your files to an external hard drive or to the cloud. 
  • Stock up on supplies. Your tools help you implement your goals and deliver your work. Make sure you always have your favorite notebooks and pens on hand. 
  • Meal plan. For those days when you don’t have time to cook, have some frozen healthy meals and other options in stock.

Written by JiJi Lee.

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