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The Keys to Answering: Is it Time to Go?

The Wall Street Journal recently published an article about Baby Boomers and the challenge they face in knowing when to retire as well as planning next moves

after retirement. This got us thinking:

it’s not only Baby Boomers considering retirement who struggle with knowing when it is time for a change. No one

wants to leave the party early and miss that moment that makes the night and no one wants to be the last one there, cleaning up the mess, wishing they were already home and asleep.

Whether you are considering retirement or simply deciding it is time for a change, gauging the optimal timing can be intimidating. Often, we work with clients who are considering big shifts; retirement, industry change, role change, or even just leaving a company where they have been for a significant amount of time.

The key to making these decisions? Awareness, preparedness, support, and resilience.

Easy, right? 😉

Before you start moving through this inventory, take some time to clarify your personal goals. Where do you want to be in one year, five – what does happiness look like to you? While we are squarely in the career advisory world and not life coaches, we know how vital it is to consider the impact work has on your personal life and vice-versa so make sure to consider what you are hoping you life looks like down the road and how changes now can play into or deter from that. Because we’re career advisors, we are only mentioning this point once! You will use your goals / desires as a compass so it is important to have them defined.


How often do you take a step back and inventory your work situation? Having a global awareness of what is happening will help you determine if this is a situation that is in alignment with your goals, values, current life stage, and down-the-road vision. Some questions to ask yourself here are:

· What is the current state of my industry?

· What is the outlook for this industry in the coming years?

· What is the organizational health like where I am? Culture, leadership (direct and

indirect), financial position, etc.? Look at this for the company, your department, your

team and individually.

· Are you happy?

· Are you challenged?

· Is there a clear path forward that aligns with your goals?

Maybe you realize you LOVE what you do and the company but are struggling with your direct leadership.

Maybe you realize the industry you’re in is evolving in a way that does not support what you want to be doing.

Maybe this step back yields the answer that where you are, is exactly where you want to be.

Regardless of the result, move through to preparedness. Things can change so quickly (thanks for the reminder of that, 2020) and having a plan in place is your insurance policy as well as a key part of establishing career resilience. Reassurance that no matter what happens, you’ve got a parachute and a way forward.


The path forward can feel uncertain and well, it is! We have control over very little so getting prepared and organized around what we can is a great way to ease the anxiety that is sure to arise with so much change and unknown.

We work with clients using a tried and true method call The Kapitalize Process to build a plan and along with that, resilience and empowerment.

The Kapitalize Process

Reflect – guess what, you are already off to the races here with your work for preparedness. Take a look back at your career, your current role and consider:

· What is working?

· What is not?

· What have you loved and hated in this role?

Reveal – Now dig deep into your experience. Here we ask clients to complete an Accomplishments & Measurements Matrix which requires you to concisely record your achievements in each role you have held. What did you do, how did you do it, and what was the outcome? This reveals what we call your Pattern of Excellence (PoE). Across each role there will be a pattern, the things you consistently excel at. Level, industry, role, career trajectory – this holds true for every client we have ever worked with.

Now compare what you have honed in on about what you want (your goals) and your PoE. Where is the intersection?

That intersection is where your magic lies. This is where you will do your best work and this is where your path forward stems from. If that path forward still exists where you are, great! Stay put and know you are prepared if anything changes. If that path forward is not possible where you are – time to make a transition plan and get moving.

Reconstruct & Revitalize

Now that you know if it is time to make a change or not, you can plan. Here we dig in and help clients create outstanding job search documents (resume, cover letter, LinkedIn, etc.) that communicate their unique PoE and what they have to offer to potential employers. We should note that there is constant interplay and tweaking within these two stages, which his why we combined them. It is critical work!


Everything is in process, as you move through job search and your career, you will continue to refine these documents and your plans. Don’t let this process be a one and done deal. Come back to it annually as a way to ground yourself in your career intentions and check in to see if your current situation is still in alignment with those.

This way, whenever it does become time to make a change, you have a structured way to be sure that is what you want to do. No more wondering, “is the timing right?”


Working through things in isolation can be challenging. Create your team of support so you have people to bounce ideas off of, trusted advisors or friends to review documents and simply listen when you’re wading through the uncertainty bound to come with change or the consideration of change.

This can also be important for accountability. Some of this work can be challenging and very easy to put off or ignore entirely. Unfortunately, sometimes this means the decision to make a change gets made for you while you were procrastinating. Bring someone into your plan who won’t be afraid to nudge you if progress is not being made.


Resilience is the reward of the hard work. Becoming aware and prepared, walking through the Kapitalize Process – this will all empower you to be able to move forward regardless of what life throws at you. Organizational restructuring, bad boss, early retirement, global pandemic…if you know your goals and your PoE, you always have a hand on the pull for your parachute – and can hopefully glide safely and blissfully into the next phase of your career.

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