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5 important questions to ask before chasing your dreams

I have loved words for as long as I can remember. There is something deeply moving about the right combination of words strung together to evoke emotion and move us from here to there. Just yesterday I took some time out to sit in a sacred space with a great book and a good cup of coffee (I’ve had better), and to read aloud a passage from A Christmas Carol by Charles Dickens. I love to read it at this time of year and there’s something about opportunities missed, and the fact that it’s never too late to make a change, that moves me deeply. I find myself in that space at the moment. I’ve decided to go study again. I say again because I already have a few degrees. And while they are useful, and they were all pursued for worthwhile reasons, I never had the opportunity to study what I most wanted to: writing. I hear you say: “Maybe that’s for the best. I mean, what would you eat?” I know, I know. Some dreams should simply remain dreams. And sometimes you have to do the sensible thing in life.

But sometimes… Just sometimes… You need to take a chance on yourself!

As I said, I have been thinking about unrequited dreams a lot lately and if I had to share 5 thoughts or questions to ask before launching into following those dreams, it would be the questions below. I didn’t derive these from any scientific process. These are simply the questions I’ve been asked and questions I’ve asked myself as I’ve tried to determine whether or not pursuing the dream I’ve had for over 30 years is madness or some divine plan, or a little bit of both. So let’s get to why you’re here:


  1. Why do I want to do this thing? What is my why?

Simon Sinek in his book “Start with Why” says the following:

“Working hard for something we do not care about is called stress, working hard for something we love is called passion.”

Sometimes we have dreams or desires that we desperately want to pursue. But if we don’t know why then we cannot discern whether or not these are dreams we SHOULD pursue. Some dreams are beautiful, but we are pursuing them for misguided reasons. Either we have a skewed/romantic view of how that dream would play out in our lives, or we are pursuing them in order to fulfil an emotional or psychological need. Sometimes, when we answer the why question, the dream becomes less important because we understand what the root of it was and we can either find healing for a negative root, or we may find that same fulfilment in a different way. Sometimes when we discover the root of the pursuit it spurs us on because we know our reason for the pursuit is good, and healthy, and grounded. So, what is your why?


  1. Do I have any pre-existing ability/talent in this area?

I love an underdog story. Whether it’s watching Rudy defy the odds after being told he’s too small to play college football, or when I hear stories of those the world has judged as “wanting” overcome impossible obstacles as they march to the beat of their own drum and make a success of whatever they do.

Sometimes it’s watching Idols or America’s got Talent and seeing someone who looks plain and unassuming get up and blow the crowd away with what they can do.

But I’ve also watched enough episodes to know that sometimes there are people trying out for Idols or AGT who have been lied to since birth by their very well-meaning mothers and told they have angelic voices that will move people to tears. And that they will, but for all the wrong reasons.

So this brings the question: “Do you show any talent/ability for the dream you want to pursue?”

Please hear me out, I believe we can learn most things quite successfully with the right process, mentorship and teaching. But I also believe you need some modicum of talent to start with. If you don’t have a predisposition to rhythm or cannot carry a tune, go ahead and give it a try, but know when to call it a day on your singing dream.

I would encourage you to give it a go. But then ask the people in your life that you know will be truly honest with you for their opinion. Here’s a hint: Don’t ask your parents.


  1. Do I love the idea of what I am pursuing more than the thing itself? Have I tried it?

Many people love the idea of writing, but have never written anything… Many shower singers have sung their solos but never pursued a career in singing. Sometimes we are drawn to something because of a preconceived idea in our minds of what our lives would be like if we were to pursue said thing. But often, the reality is far different. I’ve heard so many stories where someone has studied in a certain direction and when they start working, they discover that they hate what they’re doing. I would strongly encourage you to dip your toes into your dream space before committing to anything. If you want to write, start a blog, get your butt in your chair, and put in your hours. If you want to sing, take some lessons, attend an open mic night, and see what shakes loose. Experience the full circle of creation, exposure and criticism and then ask yourself: “Do I still want to run after this thing?” If the answer is yes, go for it!


  1. Do I have the support of my friends and family? Can I dip my toes in without giving up my day job?

Do you think your day job is the reason you cannot follow your dreams? I have some news for you: this is a lie! If you want something badly enough, nothing will keep you from it. You will write at 5 am. You will pack your gym clothes and get on the elliptical at 7 p.m. after a long day. You may even put your kids in front of an episode of Bluey or Peppa Pig while you work on that dream (please don’t judge us!) But one of the riskiest things you can do is believe the lie that you need to abandon your day job to pursue your dream. Why? Because you don’t have to. It places pressure on your family unit and takes what should be a time of exploration and fun and turns it into a stress-filled and pressured pursuit as you try to find income to pay your bills.

In his book “Quitter”, Jon Acuff writes: “Quitting a job doesn’t jump-start a dream because dreams take planning, purpose, and progress to succeed. That stuff has to happen before you quit your day job.”

If you have a great job, hold onto it! And then sit down with those you love and have a conversation about how you will find space and time to pursue your dream. Because at the end of the day, if your friends and family don’t support your pursuit, it’s unlikely to succeed anyway.


  1. Finally, ask the question: what does God say? Can I serve God in and with my pursuit?

I know not everyone who is reading this will share my faith stance, but as someone who believes in and follows God, I want His opinion. In fact, I don’t want to walk down any road He hasn’t prepared for me. Sometimes He maps out my path, sometimes I step out and trust I am doing the wise thing, knowing He will catch me if I’ve made a mistake. A friend recently spoke about our choices and how the wrong ones won’t remove us from God’s grace, but they could derail us from His preferred future for us. (To watch his full talk, head HERE) I believe this applies to pursuing our dreams as well. I know that God will be able to redeem any wrong decision I’ve made. But I also believe that I would rather have Him steer my life in order to minimise those moments. More than that, I want my life to matter. I want what I do with my time to matter. So I always ask the question: “This thing that I want to do. Can I glorify God while I do it? Can I bring Him glory through it?” And if the answer is no, then quite honestly, I shouldn’t be pursuing it. Please hear what I’m not saying: I believe God can use us in just about any vocation, space, and situation, that is, if we let Him. I know Plumbers who glorify God while they plumb – can I use plumb as a verb? I’ve seen cashiers and businessmen; art teachers and botanists glorify God in profound ways. My dream is to write. And I hope to change lives and draw people closer to God as I do…


So those are the 5. Please let me know if you’ve found them helpful and be sure to share something in the comments about your dream and what you’re doing to pursue it. I’m running after mine… How about you?


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2 Responses

  1. Dear Taiki
    There is always something profound to be found within any of your God received and shared wisdoms.
    I love the sincerity, clarity, and homely humour in which you deliver these beautiful nuggets of truths.
    God has not only enlightened you about your path, but has cleverly alighted this on persons such as myself, through your penned (typed) wisdoms.

    Recently you prayed intently with regards to this new season and path which God has started journeying me upon. And to offer that as additional feedback, l can say that His work is being made perfect and impressioned on me daily, with the new after-hours clients that He sends my way.

    Thank you for taking time to pen these wonderful steps. Thanks always for your friendship. May God continually satiate the desires, needs and unctionings of your heart. And may he continue to use this brilliant blog as a platform to steer and navigate others.

    1. Thanks Vaughan, for the too kind words.
      This was written beautifully and perhaps I am not the only one that should consider putting some pen to paper 😉
      I will keep praying, but am so glad to hear that there has been some breakthrough. May it keep coming and may God keep directing your path.
      Thanks for your friendship and support, it means the world. Keep praying for me, k? Promise to do the same. Bless you!

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