I initially wanted to title this article ‘reflection & anticipation’ because there are always two sides to planning. One simply can’t just think about the future without taking into account the past. The first portion of this article will focus primarily of reflection. This is so important in living an honest life that I would even go as far to say: reflecting is what made me who I am today.

I don’t know how many of you can relate to feeling like a robot growing up. Following orders from elders and following the next step led by society. You were told what to do and honestly, it was quite easy. We didn’t ever have to stop to think for ourselves: “well, what is true to me?”

I highly urge you to take days and even weeks to practice reflection. It’s not going to come easy and it may even drive you crazy at times. I’ve read many books on this topic and spent many a weeks pulling my hair out tired of thinking about my past. But like I said, it is what’s helped me get where I am and it is what makes goal setting much much easier. Lucky for you, I’ve created a list of questions that will help drive the thought process. Be sure to write down the answers to all of these somewhere so you can refer back to it from time to time.

What are my core values?
What or who energizes me?
What or who brings me peace?
What or who makes me angry/sad/jealous/uncomfortable?
What do you always try to avoid? Why?
What or who should I avoid in order to live a happier and more fulfilling life?
Where do family, country, and the rest of the world fit in?
Why work? What’s work for?
How does success relate to work being “good work” or not?
What is the importance of money to me?
What is worth the pain?
What will you never give up on?
What do you need most right now?
What would you immediately do differently if you knew no one would judge you?
What is something nobody could ever steal from you?
What/Who would you like to forgive right now?
What scares you? What is your biggest fear? Why?
Death is the only certain thing in life. What kind of legacy do you want to leave? What do you want to leave behind in this world?

Now that you’ve taken the time to go through and write these out, it’s time to goal set. The way we’re going to approach this is first by bigger picture thinking and then breaking it down into smaller goals. I know that sounds a bit intimidating but I will take you through it step by step.

Step 1: What’s your 100 year goal?

One of my first ever career mentors once asked me to think about my 10 year goal, my 20 year goal, my 50 year goal, and then my 100 year goal. I was perplexed. I asked him “What do you mean my 100 year goal? I’ll probably be dead.”

He smiles and replies back “Exactly. You probably will. What do you want your life to count as? What kind of legacy do you want to leave behind? What do you want the world to remember you by?”

I had never thought of that. To this day, this has been my favorite question asked to me. So I ask you: What is your 100 year goal?

It can be as simple as making sure my your family (kids, grandkids) know they were loved and taken care of. It could be providing them with generational wealth. It could be writing a book or creating a podcast to pass down your stories. It could be to help as many people as possible. It could be to create something that helps global warming. This is for you to decide what kind of impact you want to create. Dwell on this for a little bit.

Step 2: Analyze 3 different lives

Once you’ve realized what that big picture goal is, take a moment to think about how you’ll get there. You might only see one path ahead or you might see 15 different paths ahead. Either way is correct but we’re going to flex our creative muscles and either expand or narrow down to 3 different lives. I want to remind you that we’re not limited to living just one life. It often feels like we’re stuck and we can only be one persona. While we’re discussing goal-setting in this article for one particular life, know that you can revisit this exercise whenever you’re ready to make a pivot into something new. While I’m sure you already have some different lives/personas in mind but if you don’t, here’s some questions to ask yourself.

Life 1: What is the path you’re currently on?

Life 2: What is something you’d do if life 1 fails or doesn’t work out? What’s your back-up life?

Life 3: What would you do if money weren’t an object in this world?

Step 3: Creating 5 year plans

This step is going to take a little longer. We’re going to take each one of our 3 lives and expand that into 5 year plans. I believe that physically writing things down is the best way to do it. Take a piece of paper and fold it so it creates 5 equal divides. Now go in, title you’re page, and in each column title it with the next 5 years as well as your age.

First and foremost, you’ll take the big career idea of your life and turn that into a 5 year plan. Write down what you want to accomplish in year 1, 2, 3, 4, and where you see yourself in year 5 of this plan. You’ll notice this is much easier than thinking of a 100 year legacy. And 5 years is a good amount of time to dream. Plus it gives you a focus point and something to work towards.

Now this is very very important. Add in any fun life things: vacations you want to go on, races you want to be a part of, weddings, kids, celebrations, add it all in. Add in hobbies and skills you want to practice. My life things consisted of writing a book, running a marathon, scuba diving, and getting married. This is your life! Dream big and dream of things that excite you! (Wow, I’m getting excited just thinking of everything you are planning)

Repeat this process for your other 2 lives. Keep in mind how you feel while dreaming and ideating each one of these lives and write it down. On a scale of 1-10, evaluate them on: confidence, how much you love it, if you have the resources for it, and if it makes sense to who you are (goes back to the question on your core values).

In addition that, I like to keep track of any questions and thoughts that come up as well as any fears while dreaming of these lives. It’s important to write and consider those.

Step 4: Gather your board of directors & Decide

Step 4 is to contact your trusted board of directors and chat with them regarding your 3 potential lives.

A personal board of directors is a group of between five and 10 individuals that can help you make sound decisions, give you advice and feedback, challenge your assumptions, broaden your professional network, brainstorm and gut check ideas, and generally expand your perspective and thinking.

source: https://melissaeisler.com/your-personal-board-of-directors/

A lot of times our trusted ones know us more than we do. They provide an external perspective which often times can be incredibly helpful and provide insights as to what’s best for you. At the end of the day, the decision is all yours but it’s important to chat about these big life decisions with them. At last, that’s what they’re there for 😊

Schedule a 20-minute call with at least 3 people and get their thoughts. During the creation of 5 year plans and your conversations, your gut will tell you to lean towards something. Hang onto that feeling and go with that direction. Select a life and move forward with it. That’s it. Do NOT overthink this decision. You’ve already spent a lot of time on it. The questions and fears you had about this life will work themselves out. Trust yourself.

Step 5: Break your 1 year goal into actionable steps you can take today

This part should be the easiest. Now that you have a long term vision, a mid term goal, and an idea of how to get there, take that one year achievement and break it down into smaller 3 month and daily steps. Find something you can do today (or tomorrow if it’s past 10PM).

Remember to take action!! I don’t know why but a lot of people hesitate at taking action. Your life is in your control! We just spent so much crafting a life you want to live that fulfills you, energizes you, and brings you peace. Go after it!!!!

Step 6: Re-evaluate and go back to the drawing book when needed

I have a running joke with my board of directors that I’ve created a 5 year plan 4 times in the last 2 years. The reality is, life happens. Sometimes good things, sometimes bad. After all, there are things out of your control (covid anyone?) and it’s okay if life goes out of track once in a while. Remember the real reason we started goal planning. To help you focus and keep yourself accountable. To take charge of your life. If something doesn’t feel right and the life you picked isn’t right for you anymore, go back and re-do these activities. I’ve done them several times and while it can be time consuming, it really helps clarify my goals and re-align with who I am + who I want to be.

inspired by the book: Designing Your Life by Bill Burnett & Dave Evans

Goal Setting & Yearly Planning