Let’s get started with the challenge

Day 13: Consider the Big Picture

Today's Prompt:

Read the post below about designing the life that you want. Use the prompt to then think about and answer the following questions:

  1. What are the roles that are important to you in your life, and how will you prioritize them? 
  2. What are your personal financial goals? 
  3. Where would you like to spend your time? 
  4. Do you want to be an employer, managing other people, or do you want your business to remain a solo gig, where you outsource occasional tasks as needed? 

Do you want to save a certain amount of money by a certain age and have a proper retirement? Or are you comfortable with the idea of mini-retirements?

We touched upon the importance of vision in Day 1. We considered topics such as what our ideal day consists of and where in the world we would like to set up our business in Day 9. We believe that it will be a powerful exercise to focus next on Lifestyle Design.

Lifestyle Design is a concept that Tim Ferriss certainly did not invent but made popular in his book The 4-Hour Workweek[1]. He begins with the question, “How can one achieve the millionaire lifestyle of complete freedom without first having $1,000,000?” He challenges readers to break free of the 9–5 desk job mold that we so easily march ourselves into after high school, or a two- or four-year degree, and then mundanely go about our lives until the ripe retirement age of 65 (or, in many cases, older). Ferriss advocates for his readers to think about how they can create their own source or multiple sources of income that are location-agnostic so that they can break free of the mold and live the life they’ve always wanted.

While the book is motivational, and you should certainly check it out, I don’t want today’s prompt to turn into a book report. Instead, I’d like to take his term “Lifestyle Design” and present several questions for you to ask yourself related to it and explain why answering these questions is vital to starting up your business.

Presumably, you aren’t just setting up your own business or having a go at your own side-hustle for the sole purpose of making money. You are likely concentrating on a skill or subject you’re passionate about; you want to create your own hours; you want to manage how the revenue of your hard work is distributed instead of receiving a paycheck each month at a set amount from a company that isn’t yours with no “potential upside.” There are many possible reasons. But before you take a brave leap off the diving board into the pool of self-management, it’s key to understand how your life will fit around this new idea – or, better yet, how this new idea will fit around the life you want.

When I (Casey) was deciding whether to transition out of my 9–5 gig (in reality, it was a 6–6 gig), my husband and I coincidentally had lunch with our friends Dana and Zak, who own their own photography business. (I mentioned them in yesterday’s chapter about superfans.) I explained my situation to them and shared my ideas for what I would do instead if I left my job.

They told me about the ups and downs of starting their own business, confirming several times that, despite the lows, it was the best decision they had ever made. They added that one of the best practices they’ve incorporated into their business is to have a company retreat (which involves just the two of them, the sole owners/employees). On the retreat, they remove themselves from the distractions of daily life and technology for 24–48 hours. They travel to somewhere remote, where they set their goals for the upcoming year and for the longer term, discuss how their business is affecting their personal lives, and hold themselves accountable for ideas they had the previous year.

I was really inspired by this idea, so my husband and I almost immediately went away for a weekend after seeing them. Prior to the trip, we prepared questions that we would answer together while on the trip about how we wanted to design our life, financially and aesthetically, and how my new potential business ideas could fit into this ideal lifestyle.

To start thinking about how you can make the latter happen, I’ve shared the questions that we asked ourselves below. A few of the questions were adapted from The Art of Manliness post about creating a blueprint for your life[2].

What are the roles that are important to you in your life, and how will you prioritize them? 

Consider the roles that you play in your daily life, and include roles that you aspire to play. Obviously, these will shift as priorities change, but thinking about what aspects of your life are most important to you is a valuable exercise. For example, I am a…

  • Strong leader
  • Writer
  • Geologist
  • Aspiring photographer
  • Wife
  • Sister
  • Someday mother
  • Daughter/daughter-in-law
  • Friend

My husband and my family are the most important thing to me, so I don’t want to create a business for myself where I am working 12–18-hour days and unable to enjoy my life with them. Ideally, I’d like to work on a collection of projects that allows me to have the flexibility I need to spend time with the people I love.

If your professional roles are more important to you, that is absolutely great. The whole point of this question is to consider what you need to prioritize at the time you’re answering the question, and then keep revisiting your answers as they change so you can shift priorities accordingly. 

What are your personal financial goals? 

First, consider your idealistic goal – how much money do you need to be generating per year in order to live your dream life? Have you always dreamed of traveling in Asia for six to twelve months? Or owning a house on the beach? Or having enough flexibility financially that you have time and money to spend giving back to your community? Dream big – the whole point of this is to write down your idealistic goal.

When we completed the exercise, we didn’t write down a specific number we wanted to achieve in our bank account. Instead, we wrote down how much passive and active income we’d ideally like to generate per year to live the life we hope to. I would advise you structure it this way as well – it’s easier to work with a number per year than one, big number with no structured meaning. (And this question is not included because money will make you happy. We’re including it because it forces you to think about what activities you’d like to spend your time doing, where you’d like to live, how you’d like to give back to others – and all of those pieces involve money in some capacity.)

Next, consider your shorter-term, almost immediately attainable financial goals. How much money does your business need to be generating in the nearer term so that you’re comfortable making your side-hustle your full-time gig? How much money do you need to pay your bills and maintain your current lifestyle? Are there current, unnecessary expenditures that you could cut back on for now to make your switch sooner? 

Where would you like to spend your time? 

This question is simple. Have you always pictured yourself stationary, moving back to where you came from or staying put where you are now? Or do you want to be a nomad, location-agnostic? Or live in a combination of places – like spend three months per year in Hawaii and nine months per year in Scotland? (Sounds pretty great to me!)

Considering this question will help you fill in any gaps in our earlier question about your financial picture – if you want to live in Hong Kong for the rest of your life, that’s an expensive city, and you know that your business will need to generate a lot of income to do that. If you want to live in Southeast Asia, you may only need to be generating several hundred pounds or dollars per month, but then, your business itself may need to be location-agnostic. 

Do you want to be an employer, managing other people, or do you want your business to remain a solo gig, where you outsource occasional tasks as needed? 

Some people are born managers, and an attractive piece of owning their own business is the opportunity to manage others and create jobs for the community. (Personally, I love managing people, so I could envision owning a business that employed several other people someday.) Other people hate the idea of managing other people and want nothing to do with people. (Kyle will tell you he fits into this category, but I think he’s more of a people-person than he lets on.)

Either one is the right answer; it just depends on what feels natural for you. This will help you outline how you want your business to be structured. If you know that you absolutely do not ever want other employees, then any future tasks that require other people can be outsourced (see Day 27: Build Your Toolbox). If you do eventually want to manage people, then that can be a part of your business plan. 

Do you want to save a certain amount of money by a certain age and have a proper retirement? Or are you comfortable with the idea of mini-retirements? 

In Ferriss’ book, he discusses the idea of mini-retirements. Personally, I was totally excited about this concept. Essentially, he argues that, instead of building up to this inevitable “retirement” at some age set for us arbitrarily by a company or government that we work tirelessly towards during our most active years, we should consider a different option. We’re living longer, healthier lives. That means that retiring at 65 doesn’t necessarily mean that we’ll save enough money to live another 20–30 years. We’ll also likely get bored (and, thus, our health will decline) if we don’t use that time actively and productively.

Alternatively, we can work on a collection of several businesses or projects throughout our life. In between each project or business, we take “mini-retirements” that can be used for travel, relaxation, connecting with friends or loved ones – anything! Even if you do plan to work on the same business or project your whole life because you’re extremely passionate about it (which is great!), you can insist on extended break periods throughout your life.

This question isn’t so much a specific question but more of a prompt. Consider the mini-retirement concept. Does this sound attractive to you? Are you open to it? What would you do with that time? Is it feasible for you to incorporate extended breaks for travel or otherwise into your new business? (Make it so – it’s your business!) Think about this concept as you plan out your financial picture in the earlier question about financial goals.

Hopefully, these questions have helped you to start thinking about how your business will fit into the life that you want. I strongly encourage you to take a day once every few months, at the very least once a year, to disconnect from distractions and revisit your answers to these questions. We will revisit these important questions again on Day 23.

[2] McKay, B. (2017, February 16). How to Create a Life Plan in 5 Easy Steps. http://www.artofmanliness.com/2011/02/08/create-a-life-plan/. 27 Feb 2017.