This is a guest post by Colin Hiles.
As I work with mid-lifers helping them design their freedom lifestyle, I’ve noticed three common themes that connect them all. On one level there are many things that differentiate each of them – age, stage in life, background, cultural influences, values – and yet, on another level, there are some subtle similarities. The purpose of this post is to explore those similarities whilst thinking about them from your own perspective.
So, how do you know you’re ready for lifestyle design?
1. You’re asking questions…lots of them!
“Who am I?” “What do I really want out of life?” “What is my definition of success?” “How do I achieve more meaning in my life?” “What am I here to do?” “What’s standing between me and life I want?”
Many of us hit a point in our lives where we start asking questions…lots of them. The trouble is we don’t know the answers to most of them. Asking lots of questions and not knowing the answers can be very unsettling – we like to be in the know. Knowing gives our lives certainty. But if we’re going to grow, we can’t avoid asking these sorts of questions of ourselves.
At some point, we have to hold a stop sign up to life and start reflecting, otherwise we run the risk of not finding the fun, freedom and fulfilment we’re searching for. Inner questioning is a critical element of finding greater meaning and self-fulfillment. If you persist in your questioning, you will be rewarded greatly. All the good stuff – love, peace, joy, happiness, contentment etc – will be revealed to you.
In your journal and under the heading ‘My Big Life Questions’ list all the burning questions you have right now. What are the most important ones you want answers to?
Heed these wise words from Rainer Maria Rilke…
“Be patient with all that is unresolved in your heart and try to love the questions themselves. Do not seek for the answers that cannot be given. For you would not be able to live them. And the point is to live everything. Live the questions now and perhaps, without knowing it, you will live along, someday, into the answers.”
2. You’re reflecting on the past.
If we don’t want the past to equal the future, it’s important we give some thought to the past. After all, it’s our past that’s brought us to where we are right now, and whether that’s a good or bad thing, the past has to be honoured before we can move on. Moving towards our middle years may be unsettling, but it brings with it an opportunity to reflect on how we’ve played the first half of life, the decisions we’ve made, and to look at how we are going to change things starting today to make sure that we’re heading to the future we desire.
So what has happened so far? Have you lived and loved in your relationships in a way you want to in the future? Are you doing the kind of work that’s connected with your passion? Are you living beyond your means? Do you have the kind of bonds with your extended family and friends you’d like to have?
While many of us experience disappointment in the form of regrets and “what-ifs” when reflecting on our past, we must equally be willing to learn from our past – our choices and decisions that perhaps did not produce the life experiences we had hoped for. Getting answers to these questions can be very confronting, especially if you’ve invested a lot of time in your current career and you’re starting to wonder if it’s the right career for you, or maintaining your current lifestyle has put you in debt and you’re facing some big changes.
We are likely at this stage to describe ourselves as torn between two alternatives. We may feel torn between careers, one offering security and perks and the other offering challenge and heart connection. We may feel torn between lovers, unable to choose between the two, sometimes wanting both. We may feel torn between alternative lifestyles: for example, a metropolis existence with all its stresses and rewards or a simplified life with a lower income but more time in the beauty of nature.
In reality, we are torn between two selves: who we have been versus who we are becoming. This may be unsettling, but it brings with it the opportunity to think back over the decisions we’ve made and plan how we are going to change things to make sure we’re heading in the direction of a great future.
To help with moving forward, find the answers to the questions below:
What The Past Has Taught Me:
1. What have I learned from the first half of my life?
2. What lessons are there for me to see?
3. What have I learned about the world of work, bosses, and the meaning of work?
4. What have I learned about dysfunctional relationships, abusive partners and toxic friends?
5. What have I learned about my addictions? What have I learned about me as the result of the work-life choices I’ve made?
Here are some wise words from Soren Kierkegaard…
“Life can only be understood backwards, but it must be lived forwards.”
3. You’re thinking about the future.
A major task during midlife is for us to assess where we have been and to set new, appropriate goals for the future. But first we must come to terms with the inner and outer changes we are experiencing. By midlife, we are hurriedly reaching for the goals we set for ourselves in our youth. But for many mid-lifers, motivation for these youthful goals begins to dwindle. The middle years can thus be a confusing time. There may be changes in our personal values; in our appearance, self-image, physical energy, and strength.
Our relationships may be changing. We may suffer from boredom or stress on the job, or lose interest in climbing the employment ladder. We may have new responsibilities toward aging parents and lessening responsibilities toward our children. And we may have to cope with changes that come with the deaths of parents, siblings, and friends. On top of that, we are increasingly aware of the ever-decreasing number of years we have left to live. This dawning realisation can wake us up to thinking seriously about our future direction and what we want from life.
Mid-life is a time to discard what we no longer need and lighten up for the journey ahead. You can start today by asking yourself one of life’s most important questions – what do I want? Not just once, but repeatedly. It’s from this deeper exploration that our inner wisdom starts to bubble up. So does hope and optimism. It’s here that our inner journey, our deeper exploration serves us well. It’s at this point we begin to realise the gift we’re receiving – the gift of being able to be conscious and honest about where we’re choosing to go.
As we gradually move in a new direction that’s more aligned with our inner truth, we experience a life complete with true and real dignity, harmony, inner peace and a high degree of self-worth and self-esteem – something we may not have experienced that much in the first half of our life. All the answers sit inside us. If we want to make a difference in the second half of our life, it really does come down to answering this important question over and over again – what do I want?
In your journal, free up your mind and pick a date in the future, somewhere between three to five years’ time. Imagine what your ‘future perfect’ looks like and start writing about it. Write about how you are living each day. Use these questions to get started:
My Perfect Future:
1. Where am I living?
2. What does my home look like?
3. How am I spending my leisure time?
4. Who is in my life?
5. What type of work am I engaged in?
6. How much am I earning?
7. How do I feel about myself?
Be expansive and creative, no limits.
I’ll leave you with some wise words from Marsha Sinetar…
“Life’s up and downs provide windows of opportunity to determine your values and goals. Think of using all obstacles as stepping stones to build the life you want.”
I will admit doing this type of work is not always easy, but it’s always worth it. Put pen to paper and think deeply about these questions…you won’t regret it.
Please share your experiences, thoughts, and anything else in the comments.
Colin Hiles helps midlife mavericks follow their smile, find their right livelihood and create their ideal life at www.midlifemaverick.com.
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G'day! I'm Gordie, founder and editor-in-chief of Lifestyle Design For You. I want to welcome you to the center of the universe when it comes to lifestyle design and personal development blogs. We're a team of ten writers providing you with articles to help nourish your mind and improve your life. Lifestyle design is about designing your life so you can do what you want when you want.




{ 31 comments… read them below or add one }
A lovely wakeup call for those who haven’t yet started living the life they want. I think it’s so important for people to know that it’s never too late – in mid-life or beyond.
Thanks Gordie for the intro and Colin for your thoughts.
Hi Annabel,
I think it’s also good for us pre-midlifers. We can ask ourselves these questions at any point in our lives.
“What The Past Has Taught Me” This is a powerful point we sometimes miss. Napoleon hill often spoke about the power and guidance the past can offer as it can help with creating a desirable future … Thanks, great read.
The past is a great resource. Thanks, Lloyd.
Hi Annabel…I agree, it’s never to late to start living the we are meant to be living. Thanks for the kind feedback.
Hi Lloyd…thanks for highlighting an important point. It’s so important the past doesn’t equal the future. We should learn from the past not live in it. It should be a school not a burden! it’s worth asking some good questions but often we’re are to busy! Thanks for you comment.
What the past has taught me. Probably nothing most will say. History teaches us that History teaches us nothing. Very few people actually learn from their past.
If we would just take your advice and learn from our past.
Robert Bravery´s last blog ..Dear Dr Blog.
That’s so true, Robert. Look at the number of people who repeat the same mistakes and same crimes over again and again.
Fine thought provoking post!
This is really a very timely read for me, as I have been looking back and planning ahead. This is one thing that brought me to blogging, something I can do for the rest of my life.
But blogging aside, I am now on the sunset side of 50 and realize that if I am blessed to squeeze out another couple of decades I will have done well. At this point in my life I have to plan out the remainder, which means life beyond the working career and well into retirement. I simply seek to continue a life of comfort.
Life is a continual lesson to be learned from and improved upon. As this article gracefully points out, you must learn from your past experiences.
Thanks Colin and Gordie, this is a good read.

Jimi Jones´s last blog ..The Week In Review
You are a sunset, Jimi and a good looking one at that.
Like Jimi I am on the “wrong” side of 50 but I confess that I spent very little time looking back or too much time looking forward. I’m more of a Be Here Now person which stems from my old hippy days and not being able to rewrite the past or predict the future. As I get older I realise how very little total control we have of our lives. Okay I have “dreams” and maybe the old shamans were right when they say dream harder …
Kevin Tea´s last blog ..Win A Google Wave Invitation & Get More Space On Mozy
You were a hippy? I picked you more for a punk.
Thanks Robert. Point well made!
Hi Jimi, glad you enjoyed the post. 50 is the new 40!
Hi Kevin. I agree with the control point you make. I’ve also found many midlifers come to that conclusion through a life wake up call (often termed a “midlife crisis”) of some kind. At first that realisation can be a little scary for some!
Thanks you all for posing your comments. I appreciate it.
Colin Hiles´s last blog ..Post 3
Hi Colin and Gordie,
First, let me say I love Rainer Maria Rilke! Great choice of a quote, Colin.
Thanks for this post, too.
I think many of the challenges I struggle with, and see those around me struggling with, too, is seeing past success and achievement just as that, past success.
As I turn 40 next year, I look back at all the achievements I’ve reached and wonder what’s next. My world looks quite different today than my world 10 years ago, that’s for sure. I may not be clear here…I think what I’m trying to say is that I’m trying my best to not compare my past achievements with my current situation, which seems quite mediocre. It’s almost like I’m accustomed to being a high-achiever – what now?
Another way to put it: How to Olympians who win medals confront their futures, knowing striving for Olympic gold is no longer an option?
Maybe I am simply having difficulty seeing 5 years into the future?
Just food for thought.
Thanks again!
Lori´s last blog ..My Writing Experiment – The End
I’ve have to google Reiner Maria Rilke.
Many successful people don’t become really successful till their forties and fifties. In Colonel Sanders’ case it was in his sixties. You have plenty of time, Lori.
Hi Lorri,
You dilemma about being able to see 5 years into the future is very common with a lot of midlifers I work with. Be assured you are not alone!
Midlife is an important inner transition where metaphorically we come to the edge of the map we’ve been following in the first half of life and stop! This is an indication its time to start using a different guidance tool.
Put another way, it’s the transition from the head (were our maps are) to our heart (where our compass is) Now it’s time to “feel” your way forward (which looking at your blog you are doing). Let the feeling of “rightness” be your guide.
Like getting into your car at night. The road ahead is pitch black until you turn on your lights (when you connect with a feeling of rightness you’ll light up). Then, in order to illuminate more the road ahead you have to start moving.
I believe there is a period where it’s not so important to have clear goals and direction. That just keeps us in head “ideas” mode. We end up going around and around thinking should I go this way or that way?
Come out of your head and feel. On the retreat we call it our “smile on” feeling. Find “smile on” and follow it.
We all have an incredible personal trainer…its call our bodies. Let it guide.
Good luck on the road ahead.
Thank you Gordie for letting me do a guest post to your readership and to all of you who have left a comment about the post. This is a mile stone in my blogging career as it’s my first guest post.
I must apologies for my typos in the previous commnets. This is due to my challenge with dyslexia, having no one to edit, been in a rush and doing on my iPhone. That’s not one of the best combinations to have!
Please let me off!!! I promise to get better! cx
Hi Colin,
It was a great post. Thank you for contributing to our community here and being a part of it. I am very grateful.
Colin,
Great post! Thanks for sharing these reflective thoughts. Do you think midlife catches up to you, or do you catch up to midlife?
What is the definition of midlife? Is it folks in their 30′s or 40′s usually who feel their life is losing meaning and they want change?
My goal has always been to work 20 years in one profession, and then retire to do something else. 20 years would put me in my early 40′s. But then, I read about age discrimination for those in their 40′s+, which is part of the reason why I planted the Financial Samurai brand now.
Gordie – Thanks for stopping by and sharing with us your thoughts. Jesse Ventura’s thoughts are some good ones!
Best,
Sam
Financial Samurai´s last blog ..Book Review & Giveaway: “America, Welcome To The Poorhouse”
No worries. Thank you for stopping by here too.
Gordie – Can you ping Colin and see if he can come back and answer some questions? cheers
Financial Samurai´s last blog ..Book Review & Giveaway: “America, Welcome To The Poorhouse”
Sure thing. I’ll email him.
Hi Financial Samurai,
Interesting first question!
Midlife arrives for some as a soft summer breeze and for others a hurricane that knocks them off their feet and turns their world upside down.
Changes may spark a period of unrest such as a divorce, death of a parent or the process of children growing up, first becoming teenagers then leaving home for college or to live independently. Career and job changes also provide confusion and unrest.
All changes (no matter what age we are) create inner transitions (from your blog I see you’ve had a few) and transitions by nature are uncomfortable but are important for us to navigate as they bring us to the next stage of our lives.
If we pay attention to them and use this time as deep period of reflection allowing ourselves to grow in the process we will emerge out through the other side stronger, more confident and prepared to lead a more fulfilling life.
Thanks for the feedback and the interaction.
PS. I love your freedom fund idea.
PPS. Would you be up for an interview for my blog?
Hey Colin.
Very well-put article. I think that the mid-life issues you bring up are something that most of us life coaches have to deal with often, but it’s always nice to see someone else give a unique slant on it.
The following the body stuff ties in very well with Devon White’s ideas about returning over and over to the Default Self and through doing this and becoming grounded in the wisdom of the awake, relaxed body, rewriting neural pathways (neurohacking) to increase intelligence in new and wiser configurations.
Steve
Hi Steve,
I’m sure you’re probably familiar with the book, “The Answer”by John Assaraf and Murray Smith. It talked about carving out deep neural pathways in the brain to overcome negative thoughts. I learned a lot about the human brain from that book.
Hi Steve,
I’ve not heard of the work of Devon White so I’ll look him up. Sounds fascinating stuff!
It is interesting working with midlife issues…although I’ve found may are in denial of even being in midlife!
People in their mid thirties think I must be talking about people in the forties. People in their early forties think I must be talking about people in their late forties. People in their late forties think I must be talking about people in their fifties…and so it goes!!! Nobody seems to be in midlife!!!
You only have to look at the average age of death – 75 – to work it out where midlife is.
Do you find that?
Anyway, thanks dropping by and leaving a comment.
Colin
Yes,
well, maybe we should start a movement for the acceptance of mid-life, with all its multi-layered complexity. The denial stops here!!!
Hi
Just reading this trail of various comments helps me right now.
Midlife can happen anytime when your life comes to a major crossroads.
For me the combination of leaving my job (as it wasn’t right), but also to look after my elderly parents through a difficult illness for a period of 3 months, also as a single parent having two of my children moving out to their own home and University and then feeling unsure about my current relationship has presented me with such a crossroads.
The question we are advised to ask ourselves over and over again is …”What do you want?”, interestingly that is the one question I don’t have the answer to at the moment, if I did I wouldn’t be stuck at this crossroads.
However, the point about reflecting on this period, taking private time for oneself to understand how one feels and to allow the heart to take more control is well made…uncertain and uncomfortable times, but with a sense of it needing to be, in order for me to read the options on the signpost!
Thanks
Gary
Hi Gary,
It’s normal for many people to not know what you want. Sometimes one way to help answer this question is to ask what you don’t want. This sometimes helps you to focus a bit and can eventually lead you to knowing what you do want.
Thanks good point and I already have the start of a list on that subject
Best wishes
G
I know im ready to make a change – im starting up my business – making a career move! Always wanted to work for myslf!
Cool, stuff!