How to Start Over at 50 | Why It's NOT Too Late

Published on 13 May 2025 at 21:11

Starting over at 50 can feel overwhelming, and impossible…buuut it’s also a chance to embrace a completely new start in your life.

 

So season 50 or beyond is upon you… and you’re thinking (or being forced against your will) to start over? Or maybe you’re like me and the reboot was shoved at you with no say in the matter at all. Sister Friend… You are not alone, and you’re definitely not crazy for even considering it.

 

 Midlife(especially in the timeline we’re currently in, in 2025) can stir up a mix of anxiety, excitement and of course knots of fear. Maybe your career isn’t where you hoped it would be. Or you’re having to navigate a major life change – divorce, an empty nest, caring for aging parents – and wondering “What Do I Do Now?” Throw in worrying about finances, retirement, feeling dissatisfied with where things stand, and it’s no wonder Gen X is feeling allll the feels! But we’re not the first to experience this and actually it’s normal to feel a bit unsettled at this stage of the game.

 

And to be fair, making changes in our 40s and 50s can feel much harder than it was in our 20s, but trust and believe it is still very doable.. Just being here right now, you’re experiencing what I like to call it the Reboot Season.

 

 If you’re unhappy, in debt, facing a layoff, or dealing with any other struggle, remember this: it’s never too late to reinvent yourself and create a new life. Listen…I know that’s easier said than done, no reboot is ever smooth sailing…it took me almost 3 years to even BELIEVE I could start over!!

 

Starting over at 50+ does require effort and laser intention, but with the proper mindset and support, you can begin to build that life you’ve maybe put on pause… Think of this as your personal “Reboot Season” –  time to invest in yourself and charge ahead into your next rewarding next chapter.



 How to start over in life at 50

 

Asking yourself, “How do I turn my life around at 50?” can feel daunting and even a little scary. After all, the answer might involve uprooting things you’ve spent decades building. But take heart: there’s no one-size-fits-all approach to starting over at 50. Reinvention will look different for everyone. You might be changing careers while a friend is packing up to move across the country. One person might focus on personal growth, while another goes back to school or starts a business. Whatever your situation, here are some general tips to keep in mind as you begin again (whether for personal or professional reasons):

 

 Take time to self-reflect on what you want now. It’s easy to fall into routine by our 50s and put self-reflection on the back burner. But if you want positive changes, start by examining your life. What’s going well? What isn’t? How did you imagine 50 versus how it actually is? It’s okay if things feel different than you expected – maybe you feel a sense of loss or disappointment. Acknowledge those feelings. Once you accept “it is what it is” for the moment (the good and the bad), you’ll be more ready to plan for the future and figure out what truly matters to you.

 

 Make peace with your regrets. By age 50, everyone has a few regrets. To fully reset your life and move forward, it’s important to deal with those regrets rather than ignore them. Maybe you wish you had chosen a different career or handled a relationship differently. It’s normal – studies show we tend to feel the biggest regrets around areas like education, career, romance, and parenting. Confront that truth, learn from past mistakes, and then let it go. You can’t change the past, but you can learn from it. Forgive yourself where needed, and free yourself to move on.

 

 Reevaluate your career path. Many people mistakenly assume you can’t change careers at 50. That’s a myth! Ageism is real, but don’t let it stop you. Whether you want a more fulfilling job or need a higher income, it’s absolutely worth exploring your options. Update your résumé, apply for that interesting position, or even start that business you’ve been dreaming about. Leverage your experience and don’t sell yourself short. If you feel stuck, lean on your professional network for support or consider working with a career coach to brainstorm your next steps. You have decades of skills – highlight them and go for it.




Review your finances and make a plan. Your 50s are a crucial time to get a handle on your finances. Money stress can cast a shadow over every part of your life. Take a clear look at your savings, debt, and retirement plans. Do you need to revisit your retirement strategy or start one? Create a budget to track expenses and see where you can cut back. It might even help to check your credit score and build an emergency fund if you haven’t already. Getting financially organized will give you more confidence to make a big life change, especially if you’re starting over at 50 with no money saved up. (More on that scenario later.)

 

 Embrace journaling and meditation for mental clarity. Taking care of your inner world is just as important as the external changes. Journaling is a great way to increase self-awareness and improve mental health. Simply writing down your thoughts and feelings can stop them from endlessly swirling in your head. In fact, expressive writing can even boost your working memory and cognitive processing. Not a writer? Try meditation. It helps calm those automatic negative thoughts that can loop in your mind. Regular meditation can increase your focus and patience, and teach you breathing techniques to center yourself. Both journaling and meditation are simple, free habits that can reduce anxiety and help you approach your reboot with a clearer, calmer mindset.

 

 Reconnect or expand your social circle. As we get older, busy schedules and family duties often mean friendships take a backseat. But having a support network is vital when you’re making a big life change. Make an effort to nurture your relationships and reconnect with friends and family. Let people you trust know what you’re going through – you might be surprised how encouraging and helpful your good friends can be. And don’t be afraid to find new friends either.

 

Maybe join a local club, take a class, or volunteer in your community (there are often groups for people 50+). Building social support will remind you that you’re not alone and make this journey much more enjoyable.




Network and seek out new opportunities. If your reboot involves your career, networking is key. It’s a great way to open doors, whether you know exactly what you want to do next or not. Attend industry events, reach out to former colleagues, or join online groups related to your interests. Networking can spark ideas, introduce you to mentors or hiring managers, and guide you toward valuable career advice. Plus, sharing your own experience with others can build your confidence. You never know – a casual coffee chat could lead to your next big opportunity.

 

 Start with small changes and build good habits. When you’re eager for a fresh start, you might feel like you have to overhaul everything at once. Take a breath. Big transformations actually happen through small, consistent changes. You can’t reach a new destination without a road map, so begin by establishing some healthy routines. Identify one or two habits that will support your goals and start practicing them daily. For example, if you’re dealing with stress in a new job search, commit to a nightly walk or weekly yoga class to help manage anxiety. If you want to change careers, set aside an hour each day for online courses or skill practice. These little steps build momentum. Also, get clear on your passions, strengths, and weaknesses – and think about how they fit into the new life you want. Bit by bit, you’ll create a lifestyle that aligns with your vision. Remember to enjoy the process. The challenges ahead can be thrilling when you see them as adventures rather than obstacles.

 

 Prioritize exercise and health. Taking care of your health is non-negotiable, especially now. Regular exercise is fantastic for both body and mind. For people over 50, staying active can lower blood pressure and reduce the risk of serious diseases like heart disease, diabetes, and arthritis. It’s one of the best ways to keep your energy and mood up. Strength training is particularly important as we age, since our muscle strength naturally declines after our mid-30s. You don’t have to become a bodybuilder – just find an activity you enjoy, whether it’s brisk walking, swimming, dancing, or gardening. Exercise will not only help you feel better physically, but it also boosts confidence and resilience, which you’ll definitely benefit from when starting over.




 Declutter your life (literally and figuratively). A cluttered space can create a cluttered mind. Over the years, we all accumulate stuff. Take some time to declutter your living space and get rid of things that no longer serve you. Donate, sell, or toss the items that are just taking up space. According to Psychology Today, decluttering can help reduce stress, improve sleep, and even boost self-worth. There’s something incredibly freeing about simplifying your environment – it’s like lifting a weight off your shoulders. Plus, as you clear out the old, you make room for new experiences and opportunities. A clear space can signal a fresh start in your mind: out with the old, in with the new!

 

 Starting over at 50: 9 questions to ask yourself

 

Learning how to start over at 50 isn’t just about doing things differently – it’s also about rethinking what you really want from life. That requires some deep introspection. To get clearer on your path, grab a journal or find a quiet moment to ask yourself the following questions. They’re designed to help you rediscover your purpose and figure out what your ideal life looks like (both personally and professionally):

 

  1. What do I really need to be happy? (What truly brings me joy and fulfillment?)
  2. What am I doing that I don’t enjoy? (What commitments or activities might I want to let go of?)
  3. What makes me feel free? (When do I feel most myself and unrestricted?)
  4. What are my greatest strengths? (What skills and qualities do I bring to the table?)
  5. What causes or values am I most passionate about? (What do I care about deeply?)
  6. Am I willing to fully commit to my new life? (How far am I ready to go to make this change happen?)
  7. How do I imagine my life in a few years? (What’s my vision for 3, 5, 10 years down the road?)
  8. Does a potential new career or path align with my core values? (Will my reinvented life honor what’s important to me?)
  9. What’s still on my bucket list? (Which dreams or goals have I put off that I still want to tackle?)

 

Be honest with your answers – there are no right or wrong responses. The goal is to clarify what you truly want. Answering these questions will shine a light on your next steps. You might discover that what you really crave is more freedom, or that you need to eliminate certain stressors. You might reaffirm strengths you’ve forgotten or uncover passions you’ve neglected. Let these answers guide you as you design your path forward.




 How to Start Over at 50 With No Money

 

Starting over at 50 can be challenging all on its own; starting over at 50 with no money saved up or a income safety net can feel downright terrifying. Money worries are pretty common in our midlife reinvention journey. It could be that you’re between jobs, or maybe a divorce, or losing a loved one left you on a tight budget, or you simply never had the chance to build savings. The reality is that starting fresh without much cash requires extra creativity and resilience – but know that it can be done with the right strategies.

Here are some tips if you’re reinventing your life on a shoestring:

 

  1. Stay at your current job a bit longer (if possible). A steady paycheck is your friend right now. Even if you’re not happy in your job, or it's not paying what you need...try to wait it out while you lay the groundwork for your next move. That consistent income provides stability and can help you build an emergency fund or pay down debt while you plot your transition. Think of it as very temporary: you’re using this time strategically to financially prepare for your reboot. Maybe take evening courses or work on certifications for your new field while you keep earning. When you’re ready and have a plan (and some savings), you can make the jump with less risk.

 

  1. Shut down those negative Nancy's in your head, or playing the comparison game. When money is tight, it’s easy to fall into the trap of comparing yourself to others your age – “By 50, my friends have vacation homes or hefty retirement accounts…” Stop right there friend.... Comparison will only make you feel worse and isn’t helpful at all. We have to keep in mind that everyone’s journey is different, and financial setbacks can happen to anyone. Let go of the shame or embarrassment(I know easier said than done). There’s absolutely nothing to be ashamed of – we’re actually incredibly brave to reinvent ourselves now.

    Don't forget that in this journey or transition. Replace those negative thoughts with a focus on what you DO have: experience, wisdom, and the determination to STILL create a better future. A positive mindset is free(and honestly a must have) and our best weapon against ourselves...not to mention it’s powerful fuel for your journey.

 

  1. Envision “Future You” and start building toward that. Take a moment to imagine the person you want to be and the life you want to live. This vision can become your guiding star. Think about the elements of your life that have meant the most to you – can you bring more of those into this next chapter? Maybe you loved mentoring others in past jobs, or you’ve always felt happiest creating art. How can you prioritize those things moving forward? It might help to create a vision board or write out a description of your ideal life at, say, 55 or 60. Consider picking up self-directed learning in areas that interest you or that you’ve always been curious about. Set goals (big or small) that excite you and that align with doing what you love. Every step you take toward that vision – no matter how small – is building the new you.

 

  1. Highlight your transferable skills. You’ve accumulated a ton of skills over the last few decades, even if you’ve been in one field. Many of those abilities can transfer to a new career. Maybe you’re great at communication, organization, managing projects or people, problem-solving, or staying calm under pressure. These are valuable in any industry. Be sure to update your résumé to showcase these strengths. Don’t underestimate “soft skills” either – things like empathy, leadership, or adaptability. Employers are increasingly prioritizing soft skills developed through life experience, sometimes even more than technical skills. So think broadly about what you bring to the table. You might even list out all the skills you’ve gained from various jobs (and life roles like parenting or volunteering) to see how they could apply to where you want to go. Confidence in your own capabilities is key when you’re starting over at 50, especially when money is tight – it lets you pitch yourself convincingly for new opportunities.

 

  1. Learn new skills for free (or cheap). If you need to beef up your skillset for your next act, take advantage of the many free or low-cost learning resources available today. The internet is a goldmine for education. Platforms like Coursera, edX, and Udemy offer courses (often free or very affordable) on everything from technical skills to business management. For example, you can find courses taught by university professors or industry experts to help you reskill or upskill in your target field. You can learn at your own pace while still working your day job. Also, look into local community college classes or workshops; some may be free or offer discounts for adults returning to school. Continuously learning not only makes you more qualified for new opportunities, but it also boosts your confidence. You’ll feel more prepared and less anxious about the transition when you’ve equipped yourself with knowledge (and it didn’t break the bank!).

 Pros and cons of starting over at 50

 

Any big life change comes with its upsides and downsides. Starting over at 50 is no exception. It’s important to be realistic and consider both the positive outcomes and the challenges so you can prepare yourself mentally and emotionally. Here are some common pros and cons to rebooting your life in midlife:

 

Pros:

 

 You’re wiser and can make choices that prioritize your well-being. By 50, you know yourself much better. This means you can make better decisions for your emotional and mental health, choosing paths that truly suit you rather than to please others.

 You can regain a sense of control over your destiny. Instead of feeling stuck on a path you started in your 20s or 30s, a restart lets you take the wheel with intention. It’s empowering to realize you are steering your life where you want it to go.

 Your life experience is a huge asset. All those lessons learned (in careers, relationships, and personal growth) give you an edge. You can use your life experiences to your advantage, whether it’s in a new job, starting a business, or pursuing a passion. Younger folks might have energy, but you have wisdom and perspective that can lead to smarter strategies and fewer mistakes.

 You might improve your overall happiness and well-being. If you’re leaving a toxic job or lifestyle that wasn’t making you happy, starting over can dramatically boost your quality of life. Imagine doing work you love or living in a place that inspires you – your day-to-day well-being can skyrocket when you align your life with your values and passions.

 

Cons:

 

 Financial stability might be harder to maintain at first. You may have to work harder (or adjust your lifestyle) to stay financially stable, especially if you’re starting from scratch in a new field or if you tapped into savings to make the change. Budgeting and maybe tightening the belt could be necessary while you get established.

 The process can be stressful and impact your mental health. Let’s be honest: job searching or changing your life at 50 can be stressful. There might be moments of self-doubt or frustration, which can put you at risk of feeling depressed or anxious if you don’t take care of yourself. High stress levels can even affect your physical health – for instance, chronic stress is linked to issues like heart disease, high blood pressure, and more. It’s crucial to have coping strategies (like the exercise, journaling, or meditation mentioned earlier) to manage stress during this time.




Adjusting to big changes can shake your confidence. You might experience moments of imposter syndrome in a new environment. It’s common to worry “Am I too old for this?” or “Do I really belong here with all these younger folks?” Doubts can creep in when you’re out of your comfort zone. It helps to remember why you chose to start over and recognize that everyone feels like a newbie when they try something new – your feelings are normal and will likely pass as you get more experience.

 There may be extra hurdles (like age bias). While we wish it weren’t the case, age discrimination can happen. Some industries skew younger, and you might feel you have to prove yourself more. This can be discouraging and stressful. The key is not to internalize it – any employer or person who judges you solely by age is missing out on what you offer. Seek out people and places that value what all ages bring to the table. Also, stay young at heart: keep learning and stay curious, which naturally combats a lot of negative stereotypes about age.

 

Despite the cons, many midlifers say the pros outweigh the challenges once they get to the other side. With preparation and the right mindset, you can mitigate the downsides (for example, by saving up some money, practicing self-care, or seeking support from a mentor or coach). And the upsides – a happier you, living a life you love – make the journey worth it!

 

 Starting over in life at 50...But With a Community

 

Figuring out how to start over at 50 can feel overwhelming, and let's be honesty...scary.  But you shouldn't ever go it alone. I definitely started alone and didn't follow this advice *Face palm*...and treaded those lonely waters for about 2 years. Spiraling, beating myself up and blaming myself for my small businesses collapse. I believed a lie I was telling myself, because I was too embarrassed, and really sad to be honest...seeking any guidance, support or help seemed like I was accepting it all.  

 

At Reboot Season, I'm obsessed with helping you leverage and embrace change and rediscover your unique genius in this season of rediscovery. I've heard so many stories of Rebooters who at ages 40+, pick themselves up under thee most unbelievable circumstances, and turn their lives in to their Best life.  They all believed it wasn't too late for them...and pursued long lost dreams, or finished a goal that stalled in their 30's. It's never too late to pursue your potential and create a life that aligns with your purpose. 

 

I started Reboot Season, because of my own reboot story, and desperately needing a win, a change, or just a bit of encouragement. And not just from those people around me who love me, but those who have been where I am...and have found a way through it. I developed collection of questionnaires, guides, and resources to assist and guide you while you're in this Reboot Season.  Thee same tools I myself are currently using and hope will help other Gen X'ers like me, as they Reboot. 

 

You deserve the tools to help you navigate this new season of life. Explore Reboot Season or our Reboot Zone course for additional guidance on midlife reinvention, purpose-finding, and turning your “what now?” into an exciting “what’s next!”

 

Your next chapter is waiting – let’s make it THE BEST ONE YET!