The Fundamental Key to Improving Your 5-Year Plan:

Shift your focus from outcome-oriented to process-oriented

What do you think separates the people who end up feeling trapped and do nothing about it versus the people who realize they are trapped and get resourceful and find a different way?

They don’t wait until the “trigger moment” to make behavioral changes.

Throughout my life, I’ve always given a lot of thought to pathfinding and try to find the right step at every turn, but I’ve only recently started considering how to get there. It all comes down to long-term planning.

The best 5-year plans are flexible enough to grow with you, but you shouldn’t be throwing the whole thing out the window each year. Build in the right balance for modification while still leveraging its core purpose: keeping you grounded, motivated, aligned, and on track.

Your ideal 5-year plan should account for:

  • Who you want to be and what you want to do
  • How that differs from who you are and what you do right now
  • How you can be that person, every single day
  •  The new capabilities and daily tasks required to skill up over time

Don’t waste 5 years on outcome-oriented misery. Shift your focus and become process-oriented.


At age 27, when I look back at my younger self, so torn and full of fear about whether to accept a stable job offer or stand out by launching my own business, I see how having a clearer sense of direction and knowing that I was in full control of my life could have served me well.

In my experience, here’s what it takes to turn ideas into action:

  • Establishing systemic habits (and developing the discipline to maintain them)
  • Putting repeatable systems and processes in place
  • Analyzing which procedures work (and which ones don’t)

I haven’t been able to find a time machine (yet, at least), but reflecting on my own life and what I’ve learned the hard way motivates me to try my best to help others find guidance, direction, and belonging.

Whether you’re a recent college grad feeling overwhelmed, or a seasoned professional feeling lost or dissatisfied mid- (or even late!) career, it’s never too late to start thinking strategically and intentionally for the long term.


Think about how different you are now than you were at age 10. Why is that? It all comes down to autonomy. Growing up, our parents typically help guide us and lend structure to our life.

As children and teenagers, and even as young adults, K-12 and higher education dominates our schedules. Even in college, our lives as students are scheduled for us to some degree.

We can make the small-scale choices, like:

  • Picking a major
  • Deciding which classes to take
  • Finding clubs to join
  • The internships or jobs we work at simultaneously

… but at the end of the day, our lives as students are still measured in credit hours that add up to the same significance. All the years we spend on our education bring us closer to earning a degree.

As we walk across the graduation stage, very few people have a clear 5-year plan nailed down right out of college. As we venture out of the comfortable, pre-set structure of the education system into the unknown, most of us have our sights set directly on the intuitive next step ahead of them.

At this point in our lives, we must find the courage to stand out.

Typically, this focus is on getting that first job. This makes perfect sense. At that point, twenty-five years is a quarter of your entire life so far.

There are so many mental blocks that make this planning endeavor feel too hard or unachievable, but the only thing stopping you is your willingness to put in the work.

Don’t beat yourself up if you’re in the majority of people who didn’t sit down to write out a solid 5-year plan right off the bat… but don’t keep putting off doing so, either.

Planning & Assessment: Where You’re Headed Vs. Where you Want to Go

Are you feeling dissatisfied with your current role, worried about the progress you’re making (or struggling to make), or generally feeling lost or unclear on what you’re aiming for professionally?  It’s easy to feel stuck, hopeless, or simply complacent.

Nothing is stopping you from starting down the path towards the life you want, but you’re never going to get there unless you start now. Wherever you are in your professional path right now, here are actionable ways to regain agency and control.

A.   Establish a clear vision of:

  1. Current 5-Year Trajectory: Where you’re realistically going to end up over the next five years, based on where you are right now and what you’re doing every day
  2. Intentional 5-Year Plan: Where you want to end up in that timeframe, and the goals you hope to accomplish over that stretch

B.    Compare and Contrast

  1. Do these two match up?
  2. If not, how can you align them?

Here’s link to the tool I personally use; I do this every week for the buckets on my compass.

It’s critical to have a clear vision of not only where you’re aligned to go over the next five years, but also what you want to do and be along every step of the way. If this feels daunting, refocus on the idea of the one-degree pivot we covered in our last article.

Five-Year Planning for Young Professionals

Our last article covered the ins and outs of setting your trajectory by leveraging the power of incremental changes and one-degree pivots. This got me thinking about how five-year plans fit into the dynamic of an ever-changing professional landscape.

At the start of a career, it’s common to blindly plunge forward and assume the currents will sweep you towards the happiness you crave. Many young professionals today are in constant pursuit of the next big idea or next best job externally.

There are so many alluring prospects young professionals tend to chase after: everything from more money, power, and prestige to pure novelty and the excitement that comes with change.

It’s easy to lose sight of what really matters: internally.

Any job will include responsibilities and goals, but these achievements are organizational vs. personal. Within the scope of our employment, we must create structure that enriches us, and defines a sense of personal meaning, milestones, and progress.

 Ideally, Start Early. If Not, Start Now

The earlier we can map out a 5- or 10-year trajectory for ourselves, the more valuable results this plan will yield – and the sooner we’ll start to benefit. But, and this is a big one, most people don’t think or plan this way.

The decision to start living a more strategic and intentional life has no expiration date. It’s never too late to recalibrate and reset your direction whenever you need to. In fact, you should: the sooner, the better, if you realize the direction you’re headed in is no longer working for you.

There’s no time limit to this process; it’s never about age.  There’s no shame in re-routing if you’re off track, either. Opportunities to do so abound at any stage of life:

  • Taking a gap year or a semester off to work, volunteer, study, or recharge
  • Making a career change at any level of seniority
  • Taking a sabbatical to delve deep into self-discovery

If you’re willing to put in the work, you can shift your focus from outcome-oriented to process-oriented journeys.