The dark truth about a five-year plan

Ditch your five-year plan

Where do you see yourself in five years? If you’ve ever been caught off-guard by this question in an interview, you’re not alone.

The idea of a five-year plan is so popular because it promises certainty. That if we follow a linear path to success, happiness will follow.

But trying to predict the future is a losing battle. It’s impossible to know what your priorities will be a few years from now, let alone the opportunities you’ll be presented with down the line.

How a five-year plan can get you stuck

It’s great to be goal-oriented. I’m the first to let my Type-A flag fly high! Yet in my coaching practice, I see how a rigid fixation on planning your future can backfire, closing you off from important opportunities to grow.  

Many of my clients get so preoccupied trying to perfectly execute the details of their five-year plan that they get trapped in analysis paralysis, missing new directions calling their name. Others interpret setbacks as a sign of they’re a failure and give up.

The result is same: They stay stuck.

You can move forward confidently in your career without a five-year plan. You can still be successful, while doing it from a place of agility and resiliency, not pushing and forcing.

Question your “shoulds”

Before devising a plan for your career, make sure the path you’re on is actually the one you want. Stop to question if your five-year-plan is yours…or someone else’s. Are you following your passion, pursuing work that lights you up, or are you living out someone else’s definition of success?  

Watch for places you’re “shoulding” yourself when it comes to your career aspirations, such as, “I should go to grad school” or “I should take this job”, especially when your gut says otherwise.

Zoom in

The truth is that a five-year time frame is too daunting and difficult to wrap your head around, which is why five-year plans aren’t useful. How do you get started when the future is so overwhelming?

Try this more manageable thought experiment: Imagine one year from today instead. What would be different? What would stay the same?

This question helps you realize exactly where you feel stuck, but more importantly, illuminates precise areas where you need to take action.

Tinker like a scientist

Make a leap — professionally or personally — by adopting a more experimental mindset. Making small bets that you can adapt, build, or expand upon is less scary and easier to change than a strict long-term plan. Being able to see what works and what doesn’t is not only a learning experience but it also builds confidence over time — an essential skill for any professional.

When I shared this concept with my client Jenna, a graphic designer trying to transition to from agency life to running her own shop, it gave her permission to experiment with ways to grow her business while she still had the security of a full-time income.

Jenna and I created a series of 30-day goals for her to tackle, which resulted in significant, tangible progress towards her dream career quickly. Within just a few months, she had plenty of money saved and had a waitlist of clients assembled so she could hit the ground running when she left her agency job.

Reframe failure as feedback

Maybe you take a job in a new industry, but discover the hours required aren’t a fit for your lifestyle. Instead of feeling like your five-year plan is doomed or hoping the situation will magically improve, take matters into your own hands.

Talk to your boss about adjusting your schedule. Or, if you decide to leave, use this new information to refine your job search going forward. Ask hiring managers more about company culture and their approach to work-life balance, for example.

Review regularly

Build in times to reflect on what’s going right in your career and what needs changing quarterly or the first of each month.

During my personal review, I celebrate my progress, then take stock of what I’d like to accomplish next by asking myself:

  • What’s working best in my career right now?
  • What key actions or projects do I want to focus more on?
  • Is there anything I need to say no (or yes) to in order to make that happen?

Reviewing your progress on a regular cycle will ensure that your strategies don’t go stale. And that way you can be ready for whatever life throws at you.

A meaningful career is built through momentum, one courageous action at a time. Since it’s impossible to know what the future holds, set your sights on accomplishing the very next step, no matter how tiny it may seem right now. You won’t have to wait five years to know if it all worked out.


Melody Wilding

Melody Wilding is a coach and licensed social worker who helps ambitious high-achievers manage the emotional aspects of having a successful career. She also teaches Human Behavior at Hunter College in NYC. A popular speaker, Melody has delivered talks for TedX and others. 



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