Starting Over at 40: A Roadmap from Zero to Hero

Meet Gregory, a writer and the brains behind Face Dragons. He's the go-to guy for getting things done. Gregory's been living the digital nomad life in Asia for as long as anyone can remember, helping clients smash their goals. He writes on topics like software, personal knowledge management (PKM), and personal development. When he's not writing, you'll catch him at the local MMA gym, nose buried in a book, or just chilling with the family.

Starting over is difficult at any age, but the expectation that you should have your life together by age 40 makes it exceptionally more challenging starting over then. This post is a guide to take you from where you are now to where you want to be. Follow along if you’re thinking about starting over at 40.

My Story

Pre covid I ran a consultancy which focused on just this type of advice. But when the pandemic hit, and clients stopped calling, HQ decided that I was no longer needed and left me stranded in China, locked down with no job, income, or severance package. So naturally, I was angry, and despite advising people in similar circumstances for years, I’ll admit it took me a while before I started working towards starting over.

At the time, I blamed the pandemic, I blamed the company and the job market, but the truth was I was a little depressed and firmly in denial. I’m an introverted extrovert, so it comes naturally to me.

I was still living in my $1 Million rented apartment in Tianjin, still buying imported steaks and Belgium beers despite earning $0 per month. Something had to give.

As a consultant, I advised 100s of clients who wanted to change careers, get promotions, or start their own businesses. The process was almost always the same. First, we’d look at where they were, where they wanted to be, and then how to get there. It usually meant making sacrifices in the short term or taking a few steps back before going forward. It sometimes meant long periods of development and or holding on a little longer in a job they hated while building up the required funds.

Making a plan and executing it is all it takes; in this post, I want to take you through that process and create an ultimate guide for starting over at 40.

And, continue reading to the end to find out what happened to me.

First, Hold the World Back

Doing a self-assessment, developing a plan to turn your life around, and committing to making it happen requires time, mental space, and bandwidth. You will not be able to do it on your lunch break at work or while juggling the kids or other engagements. So you need to hold the world back while you put yourself together.

How long do you need? I’d start with a weekend. That’s a whole weekend, doing nothing else but working on yourself. If you have a partner and kids, ask them to go to Grandma’s for the weekend. Explain to your partner why you need this time and what you plan to do with it.

1. Accepting Where you Are: The First Step

Accepting that you’ve made mistakes in life or that things haven’t gone the way you hoped is far from easy, but it’s the first step to starting over. You might be thinking, “I know my life sucks right now; what more is there to accept?” but you won’t be able to get to where you’re going until you pinpoint precisely where you are.

Find something to write on and get honest with yourself about your current situation. Then, you can use it as a starting point for growth. You may have feelings pop up, seemingly from nowhere, as you take a hard look at where you are in life, don’t push them down.

Be angry, feel disappointed or guilty, or regretful it’s all part of accepting where your 40 years have gotten you, and it’s the first step to starting over.

  • Job
  • Finance
  • Family
  • Diet
  • Fitness
  • Possessions
  • Lifestyle
  • Social life

After reading the 4-hour workweek years ago, I decided to track my time for an entire week—everything I did, from when I woke up in the morning till I went to bed. The results shocked me to my core. Most days, I’d spend more time on the subway commuting to work than playing with my son.

If it weren’t for that one exercise of tracking my week and how I spent my time, I probably would still be in that job or another like it. Instead, I found another job and insisted on working from home when I didn’t need to be in the office. Eventually, I could transition to working entirely from home, which improved my relationships with my family and made me a happier, less stressed person.

Tracking how you spend your time is just one of the ways you can clearly see where you are; it’s an essential part of a self-assessment.

2. Write Down What You Really Want

Most likely, the first thing that comes to mind is where you’d like to be financially, be specific and realistic and write it down to crystalize it. Then, use the economic assessment above to clarify how much you’d need to make each month.

Once you have a goal written down for that first most important thing (it doesn’t necessarily need to be finance related), go through the rest of your self-assessment and make goals for every area of your life.

The top three goals of 40-year-olds that want to change their lives are:

  1. More money
  2. More free time
  3. More time with family

3. Make a Decision, Make a Plan

Now you know where you are, and you know where you want to be, it’s time to make a plan to get there.

You might not know how to do what you want; that’s to be expected. If you want to set up a website or your own business, it’s OK not to know how to go about it. If you want to get a higher-paying job or become healthier, it’s OK if you don’t know the steps you need to take.

You can find a way to get there if you know what you want.

Start by committing just to learning what you need to know. There are free and paid resources everywhere, accessible to you right now; you just need to look for them.

  • YouTube
  • Informational Blogs & Websites
  • Udemy, Skillshare
  • One-on-one coaches
  • Books

4. Action! You’ve Gotta Do it!

Anyone can make a plan, but a plan is nothing without action. Action isn’t easy, though, in fact, action is so challenging that I created a dragon called inaction to battle. Inaction is almost always the reason your plans don’t come to fruition. So you have to face the dragon of inaction!


We all have those days when we feel like doing nothing, tired, stressed out, and want to kick back and do nothing all day. It’s easy to say you should do it anyway, but that isn’t how we feel. You need a strategy to motivate yourself. Here are some motivational strategies you can try:

  • Youtube motivation
  • Affirmations
  • Your vision of the future
  • Look at your list of goals
  • Vision boarding

Break it down

Whenever you have a big goal or something you want to achieve, like starting a new life, the size of the mountain ahead of you can make it seem insurmountable. But you don; ‘t need to summit the mountain today; you don’t even need to start climbing. Today you can get your climbing gear in order and when you do start climbing, focus on the first low ledge.

By breaking the goal of turning my life around into smaller, easier-to-manage steps like reducing my spending, you’ll find you can make progress without it feeling like the world is on your shoulders.

Start Small

Even after you’ve broken down your goal into bite-size chunks, it can be tough to know where to start; my advice is to start small, really small. Start with something so easy it almost seems silly. Why?

  • There’s no chance of falling at the start line
  • You make immediate progress
  • The progress will give you the confidence and motivation to do something a little bigger tomorrow.

So if you want to reduce your spending, instead of selling your car and getting a bus pass, why not try saving money by not eating out? Can we break that down even further? Spend an hour meal prepping. Can we break that down? Write a list of foods to buy so I can meal prep tomorrow.

It may seem like a tiny step towards your goal of reducing your expenses which is part of an even bigger plan to create a new lifestyle. But it is a step in the right direction. Once you start moving in the right direction, the momentum will keep you going, and you’ll take faster and more significant steps. But at first, start small.

How to Plan a Career Change

When people say they want to start over, they often mean they want to make big changes to their work life. And who could blame them? The average person will spend 90,000 hours at work in their lifetime. Take a second to think about that.

By midlife, most people think they’ll have it all figured out, but some of us are late bloomers, and some of us suffer from burnout and need to start a new life.

1. Self Assessment

Start with a career assessment and evaluate your strengths, weaknesses, accomplishments, and work experience. Don’t skip this step! You will find that you have resources and skills that you can use when you start your job search or next career move.

2. Write Down What You Want

Come up with some dream jobs and write them down; even if you think they are unrealistic or impossible, they may trigger the idea that turns into your new life. For example, maybe deep down, you want to be a UFC fighter, but you might still be happy teaching kickboxing in a local club.

3. Make a Decision, Make a Plan

Once you have the idea, commit to it. Research online the skills, experience, and contacts you’ll need to make it become a reality. Give yourself a time frame to achieve each and make your career change.

4. Action

Do you need to start with a period of learning and gaining new skills? Break them down into simple steps like signup for an online sales course and make that all you have to do for today; it’s easy and guaranteed progress.

Keep your vision of your end goal in mind; stick it to the wall or in your planner, so if you have a long road ahead, you don’t quit halfway. One of my clients spent a whole year before changing her career and starting her own business.

Helen’s Story

Helen (not her real name) sold financial products in a bank in Beijing; it was high pressure, high stress, and she’d had enough of it. So when she first came to us for consulting, she wanted to be promoted into management, but after doing a thorough career assessment, Helen realized she didn’t want a promotion; she wanted out.

We went through her whole life together to come up with ideas for her career pivot. At last, she realized the only time she had been happy in the previous few years was when she was doing yoga on Friday evenings. I asked her what she’d be willing to give up to do yoga every day.

She dismissed the idea, saying she enjoyed doing it but really wasn’t that good or qualified to start a yoga studio or teach others. I told her to look back at her career assessment, “sales skills” was underlined. I pointed, “That’s what you need to run a successful yoga studio.” I could see cogs turning.

When she came back to see me a week or two later, she said all she’d been doing outside of work was yoga. For the first time, she was starting to believe that she could have a different life.

We researched yoga teacher training centers that would give her the qualifications and confidence she needed. Finally, we found one in Bali, it was well known in yoga circles and unique compared to what was on offer in Beijing.

She stuck at her job for six more months, cutting her spending and saving everything she could.

Then one day, I got an email from her; she was in Bali getting her teaching certificate. She eventually came back and opened a small yoga studio in Beijing.

How to Change Your Financial Situation

Over 60% of Americans are living paycheck to paycheck. It’s a tough pill to swallow living in the wealthiest country on Earth. But, while we can’t change the financial lives of everyone, it doesn’t have to be this way for you.

1. Self Assessment

It all starts with a financial assessment (do you see a theme here?), use the self-assessment PDF, print it out, and take some time filling it in. Your financial situation is complex, and you can’t analyze it all in your head; you need to get it on paper.

2. Write Down What You Want

Once you have the assessment, look at the numbers and decide what you want, to make more money or to spend less. It may seem foolish; of course, you want to earn more money, but do you?

Earning more means more time and effort spent on making money. Spending less can give you more money in your bank each month, and you don’t have to do anything for it.

3. Make a Decision, Make a Plan

If you decide you want to make more money, it’s time to start researching side gigs, freelancing, starting a business, and other money-making ideas. They’re all possible if you put the time into them.

Suppose you decide to spend less track your spending for an entire month (if you haven’t already) and determine what you want to cut out. Then, ask yourself, what else could you live without?

Once you have made your decision and know how you’re going to implement it, it’s time for action.

4. Action

Break your task down, start small and keep yourself motivated. If you decide you want to make more money by starting a blog, for example, don’t try to build a blog. Instead, break it down and start small!

  1. Get Hosting
  2. Buy a domain
  3. Choose a theme
  4. Pick a niche
  5. etc.

Telling yourself, “I need to build a blog this weekend,” is stressful and likely to result in you giving up, but doing a list of short tasks seems easy.

Remember, nobody found success in one day. Whether you want financial freedom or to start saving more, it’s a long-term process. So you need something to keep you motivated.

  • The thought of early retirement
  • Having a high net-worth
  • Being able to pay off your debts
  • Being able to quit your job

Whatever it is that will keep you motivated to hit your financial goals, keep it in the forefront of your mind.

So What Happened to Me?

When I finally came to my senses, I took stock of my life, what I had, and what I wanted to do. This was my self-assessment. The first thing to go was my beautiful apartment, it felt like a huge step back in life, but I knew it was what I needed to do to move forward. So I moved to a smaller apartment which cost a third of my previous one.

I decided to try making money from one of my passions—baking. So I set up a small crumpet business out of my kitchen and shared a poster on social media. The response was unexpected. I made crumpets for 10 hours a day for the next two months.

Despite improving efficiency, making crumpets was far too time intensive, and after a hard year in the kitchen, I decided to hang up my apron. I had another idea.

This website was born, it’s a culmination of my skills and experience (everything from my self-assessment), and it’s also how I managed to start over at 40.

Tips for Starting Over at 40

Reduce your Expenses and Start Saving

If you haven’t done so already, tracking your expenses (every penny!) for a week or, better yet, a month is the best way to reduce how much you spend each month. Simply tracking what you spend will make you start to spend less.

Starting over, and turning your life into something you would be proud of, will take commitment and persistence, but it will also take money! Get into the mindset of, “I’m going to sacrifice now so I can be who I want to be later.” You may need to take a pay cut if you want to start a new career, or you may have a period of earning nothing as you learn the skills you need to start a new job.

If you want to create a business, even one on the side of your actual job, you will need capital to invest.

Want to make a go of becoming fit and healthy? You might need to hire a trainer or spend more on nutritious foods.

You need money to do whatever you’re trying to achieve to turn your life around. So decide now that you’re going into sacrifice mode. It won’t be forever.

  • Move back in with your parents – it’s sad, but you’ll save so much on rent.
  • Cook all your meals – healthier and cheaper.
  • Stop buying cups of coffee – a cup of coffee you make yourself costs pennies.
  • Sell possessions you don’t need anymore.
  • Move somewhere cheaper – it may seem insane, but you can live on $7,000/year in Thailand. If you’re not earning anything while you build a business or learn new skills, why pay first-world living expenses?
  • Stop subscribing! – How many subscription services do you pay for each month? Could you live without them?

Build Your Income Every Single Day

Though your first instinct to earn more may be to find a higher-paying job, don’t count out the possibility of creating passive income or building your own business.

Even working on a side hustle for one hour a day will produce results to supplement your income after a year or two. Explore the options and commit to working on one daily till you see results.

See Your Age as a Plus

Though it might not feel like it, you have learned a lot over the years that employers find valuable and that give you a massive advantage over your younger counterparts. They know how to use social media and the latest video-sharing apps. But imagine walking into a bank, a carlot, or a financial advisor’s office. Would you rather speak to the forty-year-old behind the desk or a 20-year-old who can barely grow a beard?

Employers are aware of the authority age gives you; it signals experience and competency. You can learn to use TikTok, but they can’t instantly become older.

Get in Shape

When you have money troubles and are struggling in other parts of your life, it’s easy to see working out or getting exercise as expendable, but that’s not the right way to think about it. Instead, working out is a tool you can use to improve everything you do.

  • Better-looking people are more employable.
  • Gain More energy for working on your business or side hustle.
  • Get More focus for learning the skills you need to turn your life around.
  • More confidence will improve your relationships.

There’s a catch, though, you’re not going to get any of these benefits immediately, but starting now will get you all the benefits a year down the road. So try not to see it as a chore but as a game. Pick something that doesn’t make you miserable and keep doing it; daily is best.

If you hate to run, don’t force yourself to get on a treadmill, that’s not going to last. Why not try a boxing class instead?

Make a Fresh Start

There is always the option to make a completely fresh start, break free and create a brand new life for yourself. If you are 40 and have no partner, a job you hate, no job at all, and no real ties to where you are, why stay there?

There are so many opportunities that you could be chasing in other countries. I have been living in Asia for 15 years now, my expenses are low, much lower than back home, and as a native English speaker, I get job offers all the time. Teaching English is an ever-present opportunity out here, and it pays well compared to the price of living. But it’s not the only option:

Final Thought

All that’s left is for you to get started!