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Starting over at any age can be difficult, but starting over alone at 50 with nothing can feel like an insurmountable obstacle. Whether it be due to a divorce, job loss, or other life circumstances, it’s never too late to start over and make changes for the better.

The key to starting over with nothing is to ask yourself deep, introspective questions that will allow you to gain clarity on your values, beliefs, and goals. Take a calm moment to begin. Here are 15 deep questions to ask yourself if you’re starting over alone at 50 with nothing.

What Are My Core Values?

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When you’ve lost everything, it’s important to remember what’s important to you. Take some time to reflect on your core values. Core values are personal ethics or ideals that guide you when making decisions, building relationships, and solving problems.

What motivates you? What brings you joy? What are the beliefs that guide your life? Knowing your core values will help you make decisions that align with your beliefs.

What Are My Strengths and Weaknesses?

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Knowing your strengths and weaknesses will help you decide which areas you need to improve upon and which areas you should focus on. Make a list of your strengths and weaknesses and see where you can improve.

Common strengths include leadership, communication, and writing skills. Common weaknesses include fear of public speaking, lack of experience with software or a program, or difficulty with taking criticism.

What Are My Goals?

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Without goals, it’s hard to get anywhere in life. Take some time to set some personal and professional goals for yourself. Make sure your goals are specific, measurable, achievable, relevant, and time-bound.

Review the goals that motivate you and write them down to make them feel tangible. Then, plan the steps you must take to realize your goal or goals and cross off each one as you work through them.

What Is My Vision for My Future?

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Having a vision for your future will help you stay motivated and stay on track. Visualize where you want to be in a few years and think about what steps you need to take to get there. Vision gives direction and a glimpse over our lives to make our goals and purpose become a reality.

We must have a clear vision of our lives in order to understand where we want to be in life and where we want to be headed.

What Is My Purpose?

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While the term purpose is slightly overrated, it still holds some weight. When our circumstances change, we may struggle with redefining our purpose and can feel unfulfilled as a result. What is your reason for being? What is your calling in life?

Knowing your purpose will help you stay focused and motivated, even when things get tough. Most people start to understand and know their purpose around the age of 50 or 60, so you are not at all late to find it.

What Are My Fears?

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Everyone has fears. A situation or thing that makes you feel unsure or unsafe. Fear arises with the threat of harm, either physical, emotional, or psychological, real or imagined. While traditionally considered a “negative” emotion, fear actually serves an important role in keeping us safe as it mobilizes us to cope with potential danger.

It’s important to acknowledge them and face them head-on. What are you afraid of? Why? What steps can you take to overcome your fears?

What Are My Priorities?

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When you’re starting over with nothing, it’s important to prioritize your needs. What are the most important things in your life right now? Make a list of your priorities and focus on them. Your first and foremost priority in life should be YOU. Not in a selfish and self-centered manner, but with self-compassion and understanding. Prioritizing self-care means investing in activities and habits that nurture the body and mind.

Who Can I Turn to For Help?

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No one can do it alone. Building a support system is critical when starting over with nothing. Reach out to family and friends, or seek out a professional support group. Online forums, support groups, therapists, clubs, hotlines, and religious organizations can also be helpful.

Having open conversations with others is invaluable for mental health. It will help you exteriorize your inner concerns and find an easier solution that perhaps you were not able to see by yourself.

What Are My Boundaries?

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Setting boundaries is important for maintaining healthy relationships and avoiding burnout. Take the time to set boundaries for yourself and stick to them. Boundaries are healthy, and they are good for friends, family, partners and coworkers.

Some people have comfort from how others perceive them and may avoid boundaries in order to please others, but this is not right, and you should always draw a line when you feel uncomfortable.

What Does Success Mean to Me?

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Success means something different to everyone. It means achieving desired visions and planned goals. Furthermore, success can be a certain social status that describes a prosperous person who could also have gained fame for its favorable outcome.

Take some time to define success for you. Is it financial stability? Happiness? Doing meaningful work? Once you know what success means to you, you can work towards achieving it.

What Brings Me Joy

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For years, you’ve worked hard to make everyone happy but yourself. So what about you? What are some of the things you really want to do that will make you happy?

Get out a pad and pen and start jotting them down as they come to mind. It could be little things like petting a puppy or gardening or big things like helping seniors. Write it all out and meditate on what else you could be doing that could bring you happiness.

What Will Give Me the Greatest Amount of Freedom

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You’ve been tied down and chained your entire life. You definitely don’t want to live like that for the last 50 years of your life. Think about what kinds of things you can do that you can make a living and allow you great freedom.

Freelance writing is one idea. Travel photography is another. Or maybe you want to do missionary work. Put on your thinking cap for this one, and don’t be inhibited by technology or another language; those are things that can be learned.

What Can I Do to Help Others

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What value can you add to the world or to someone else’s life? Surely, you must have one skill or gift that will help someone or some organization.

You can direct a forum with your special skill set or do private lessons. You can also advise a company on a specific matter and train a group of people with your expertise. Maybe you are a great seamstress. There are ways to use this skill to make a living and help others at the same time.

What Am I Really Good at?

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You have to make a living and support yourself, but you also want to enjoy doing it. At this stage of the game, we don’t want a job that is going to suck the life out of us. So what kinds of things are you really good at that you can make a living doing? Think about this for one second – someone somewhere in the world is making a living doing something you really love doing.

Usually, it is hard for us to understand and notice what we are good for; apart from the obvious, get together with some loved ones, and perhaps they can tell you what you stand out for.

What Am I Really Passionate About?

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What sets your heart and soul on fire and brings you the greatest amount of joy? We often spend our whole lives just doing whatever we can to make a living and not really what we are passionate about.

Maybe you really do love petting puppies or hanging around 4 legged furry guys. How can you do this and make money? Remember, anything is possible with enough determination and perseverance.


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Starting over alone at 50 with nothing is not easy, but it’s possible. These 15 deep questions will help you gain clarity and focus as you embark on this new journey. Remember to take it one day at a time and be patient with yourself.

Starting over is a process, and it takes time. With hard work, determination, and a little self-reflection, you can create a new life that honors your values, beliefs, and goals. Don’t give up.

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