"The biggest adventure you can take is to live the life of your dreams". Oprah Winfrey

Five years is long, but not too long.

It's long enough in the future that you have time to create a path that will take you to significant milestones and achievements, but it's not so far that you can ignore them.

Even with a 100 day plan it's easy to get caught up in goals that feel urgent or have a quicker payoff. Taking a long view can be more challenging but can also be more rewarding, there's a certain sense of relaxation that comes with knowing you have time to make big plans. There's a joy in delving into our imagination and we can tap into courage, so we can be bold enough to not only envision and commit to the life we want, but set out a detailed plan to make it a reality.

This can be challenging, but the payoffs are enormous. It's also true that if we don't envision what we want, we may get there inadvertently, but the chances are low. 

Broad and specific details.

A 5-year plan is a balance of broad goals and dreams with specific details of how to get there. A broad goal may be create a life with someone, to travel, have a family; a specific goal may be to build a house, do a trip, start a garden.  

For broad goals, first, think about your life as a whole: Family, friends, vocation, calling, education, health, wealth, happiness, dreams, hopes and aspirations.

Broad goals: Some questions to stir the imagination

  • What values do you hold? Another way of asking this question is, What is important to you? Some examples could be; freedom, security, harmony, adventure, animal welfare, education, care of environment, health, contribution, community. (Note - some of these can be combined)
  • What do you want it to look like? Think in broad lifetime ideals, such as health, wealth, adventure, spirtual peace, experiences you want to have, following a calling, creating a career, producing a body of work, becoming an academic, owning your own business or having a family. (Note, some of these can be combined and combining them can actually strengthen each individually and as a whole). 
  • How can you live these goals in the next five years? Begin a health program, go on an expedition, start a business, save money, travel to destinations, begin a course of study, join a church or spiritual group, do a meditation retreat, start a running group, begin a journal, write a book.
  • What do you wish were different about your life now? Health, career, wealth, relationships, family, travel, hobbies, education or learning, where you live, who you live with? 
  • How do you want those things to be different in five years?
  • What goals/milestones do you want to reach?
  • What experiences do you want to have?

Boiling down broad goals to decide concrete actions.

Once you have your broad ideas and goals (health, adventure, family, wealth, etc.) and your concrete 5-year goals (start a business, go on a long trip, build a house, run a marathon, start a club) break them down further.

If you want to spend three months hiking through Nepal, a winter as a ski-patrol or a year building a cabin (one of my personal goals), what will you need to do to make that happen? Save money, get in shape, take a certification, learn a language, accumulate enough vacation time, take a leave of absence?

Setting deadlines

Break each of those down even further and set deadlines. Create action items that will help you reach each of these goals. For example (I'll share a personal goal, which is to build a small home in a nature setting): 

Broad Goal(s): Adventure, Security, Health, Relationship, Peace, Spiritual and Physical Health

Specific Goal: Build a home.  

What Do I Need To Make This Happen? 

  1. Figure out phases of plan. a, Build tiny home. b, Look for land. c, Acquire land. d, Move tiny home onto land. e, Build home while living onsite. f, Use tiny house for office/studio/guest house.  
  2. Save money (increase earnings while decreasing expenses). 
  3. Create financial plan for project.
  4. Decide how much time it will take to research and build.
  5. Create time line with milestones. i,e, tiny house finished by March 2017, land acquired by Sept 2017, start building house Feb 2018, house finished by October 2018
  6. Understand SWOT. Strengths, weaknesses, threats, opportunities. Make detailed lists of all of these.
  7. Consider and explore how this will effect other goals; business, health, growth, relationships, other opportunities etc.     
  8. Review all the upsides and downsides before committing to begin. 
  9. Chose start date for project  

 Here is a more generic list that can be applied to any planning process:

  • Name the goal. What is it? Be specific. 
  • Resources/Money. Estimate how much money you will need, how will you save or earn this amount and by when you will have it.
  • Knowledge. Research everything I can about my goal.
  • Timing. Research how to create time vacation policies, leave of absence, change or leave job.
  • Help: Consider resources.
  • Who: Decide whether you want to do your project solo or with other(s). 
  • Why? Why do I want to do this. This could be the key question that inspires. 

Do this for each of the broad goals that are important to you along with their corresponding 5-year goals. The more detailed your plan is - the more likely you are to see it to completion. Take your 5-year goals and break them down into year by year steps and deadlines.

Here is the real power of the five year plan:

Once you have broken year one down into monthly goals starting with the current or next month, you can make some hardcore decisions. "What will I do this week? What will tomorrow look like? What can I do exactly right now that will get me started?" 

It takes one step to overcome inertia. Two steps to create momentum.

Trust your intuition on this, if you know you want something you can begin planning right now. If you have a plan in place, you can start right now. The beauty of planning and starting plans, is that once it's committed to, all sorts of simple and wild things will happen to cause it's success. 

Revisit The Plan Often

A plan is a tool. Have a way of keeping it handy, in a book, on your phone, computer, desktop, fridge, wall or someplace you can access it. Personally, a copy my of my cabin/house action-plan is written on my bathroom mirror with wax pencils. This way I'm guaranteed to review it at least twice per day while I brush my teeth and the pencils are in the toothbrush holder, so it's easy to add to it. 

Revisit your 5-year plan at regularly scheduled times to see if your plan is working or your goals have changed and to remind yourself what you're working towards. As you grow and change, your plan will do so as well, while helping you stay focused on your long-term goals. The purpose here is progress and growth. A good method of review is to quickly (two minutes) 'bracket' the plan. Starting with lifetime, think 20 years, 10 years, 5 years, 1 year, 6 months, 3 months, 1 month, this week, today, right now.

What you do right now really counts.    


A 5-year plan doesn't tie you down, but frees up energy to to build the life you really want. It's exciting, it creates joy, purpose, opportunity, flexibility, courage, problem-solving, solutions and serenity.

It's a dream, but with a deadline.