Is Your Life On Track? 3 Questions to Ask Yourself at 30, 40 and 50 to Find Out

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Kayla Heisler1.16k
June 25, 2024 at 9:43PM UTC

As the saying goes, life is what happens when you’re busy making other plans. It’s easy to get off course. Just as life evolves, so too should the questions you ask yourself to make sure you’re on track to live the life you want.

Whenever you're approaching a new decade (or even more frequently!), see it as an opportunity to check in with yourself. The following questions aren't always the most comfortable to sit with, but avoiding them can lead to a disconnect between where you are and where you want to be. 

Questions to ask yourself at 30:

1. Where do I want to be now, next year, and in five years?

Your 20s are a time for learning and testing things out. As a 30 year old, you should have gained experience traveling down multiple areas of life to help determine what is the best fit for you. Though your answers may shift as you continue to accumulate knowledge and experiences, establishing a game plan will help see a solid plan that you can modify as needed.

2. What steps am I taking to achieve my goals?

Have a solid plan in place and make sure that you are taking actionable steps toward the goals you’ve laid out for yourself. If your goal is to retire at age 60, are your monthly retirement plan contributions making this dream feasible? If you’ve created a bucket list of countries you want to visit, are you booking flights and scheduling time off? Lay the groundwork so the moves you make throughout your thirties are in service of these goals.

3. How can I avoid repeating past mistakes?

Life is all about trial and error. Evaluate areas of your life where you wish you’d done things differently and actively work to make different choices. You don’t have to dwell in the space of regret, but take time to let the lessons you’ve learned sink in. This will help keep you on course to make choices that are better for you down the road.

Questions to ask yourself at 40:

1. What brings me the most joy?

Throughout your 30s, enjoying new experiences can show you what areas of your life you want to continue leaning into and where you want to take a step back. Taking an honest inventory of what moments have been the most fulfilling can help you choose where you expend your energy.

2. How did I accomplish my largest successes

If insanity is repeating the same thing and expecting different results, then when you want the same results, study what you did to get those results and keep doing it. Run through why certain plans worked out and keep following that line of thinking. You will likely be able to transfer the skill set into other areas of your life as well and stay on track.

3. When will I make my next move?

Knowing not only what you want to do but when you want to execute it is crucial. Early in your career, you can gain a sense that everything has to happen immediately. The sense of urgency can be daunting. After having time to gain perspective, you can better plan out what you want to do. Enjoying the comforts of what you’ve accumulated so far and striving to earn more is a delicate balance. You need to decide what really works for you and when to strike.

Questions to ask yourself at 50:

1. What skills do I need to refine?

After accumulating many skills and life experience, it’s important to never stop learning. Being in the workforce means that you want to keep skills sharp. Technology is constantly advancing, and you should advance with it. Stay up-to-date on how things have changed in the fields you work in professionally and personally.

2. How am I sharing my knowledge?

Creating a stream of information is important to share with other people. If you are working towards a specific way to work. Sharing what you know whether personal or professional can be a great way to keep working towards the goals you have for yourself. Reaching out to others can enrich your life and shine light on what areas you want to continue to focus on.

3. Who do I turn to for guidance?

While it’s common to seek out mentorship when first beginning your career, having a steady source of support is still important as life goes on. Having a person who can give you advice and listen to you as you make choices to navigate new choices in your life can be a major help.


Kayla Heisler is an essayist and Pushcart Prize-nominated poet. She is an MFA candidate at Columbia University, and her work appears in New York's Best Emerging Poets 2017 anthology.

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