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7 Questions To Ask Yourself Before You Can Start Living Your Dream Life

Download my FREE ‘Dream Life Questions’ Resource below so you can start living your dream life!

Something that became very clear to me when I was sitting in the school library, stressing about which subjects to choose for my senior years of high school was this : I had no idea whose life I was living.

Now granted at age 15 I didn’t put much thoughtful consideration into the kind of life I truly wanted to live versus the life that I thought was the picture-perfect definition of “a good life”. The “good life” to me, at age 15 was being able to have a job, earn money, eventually afford a home and start a family. It involved spending time with family and friends and getting to travel the world. And while a lot of these themes endured over the years, I can definitely say that there are key details that have changed.

I was convinced that I would go into medicine or law, not because I wanted to lean into the Asian stereotype, but because the thought, “how impressive would it be if I was a doctor/lawyer?” popped into my head multiple times.

I imagined that I wouldn’t be happy unless I had an arbitrary, self-imposed 6 to 7 figure dollar amount in my account but no real idea why I needed that much money.

I read so many books, articles and blog posts about finding your passion and ways to decide what to do with your life. Below are some of the questions that I’ve found helpful when I started trying to figure out what my dream life would look like. I’ve also created a free Dream Life Questions Worksheet that you can download below. I highly recommend using the worksheet because writing things out by hand is much better for exploring your inner-most thoughts.

Plus, it’ll get you away from your technology so you don’t get distracted. This 15-30 minute investment of your time now can help ensure that future time investments are going towards your dream life.

Sam’s Dream Life Questions

Question 1: What makes me so excited that I can’t wait to wake up in the morning?

Think Christmas Eve, the night before a big holiday or an epic event with friends. You know the feeling that I’m talking about – where you might have woken up to your alarm (or even before!) with eyes wide open, ready to physically jump out of bed with excitement. 

Now I’ll admit, I’m not feeling this way about my current full-time job. I do however feel that way about setting up this whole online community and blog, so much so that I’ve made time in the morning before work to get all of this up and running. It’s been a bit of a challenge to manage this alongside full-time work, but the fact that I work hard to make it work is how I know that this is all worth it to me.

When reflecting about this question, try and remember certain feelings first (e.g. excitement, inspiration, motivation), and then go back to try and find memories of those feelings. 

Feelings are what make memories stronger, so start with how you feel then work your way back to events and situations you remember.

Question 2. What makes me so excited that I long for more time to spend doing it?

Now I know that I mentioned not feeling the “jump out of bed in the morning” feeling about my full-time job, but there are many benefits and rewards that I’ve gotten out of investing in this experience for the time being. And while I can’t say that I long for more time doing certain aspects of the job, there are projects within my job that revolve around teaching, content creation and providing resources to help train my colleagues and get us functioning to the best of our ability. Sound a little familiar?

This was a positive sign for me, and it really reiterated the kind of work that I want to spend my time doing. 

When you’re reflecting on this question, try not to focus too hard on scenarios but rather think specifically about the actions that you’re taking. Do you like writing and creating content? Do you like designing on paper or using technology? Are you in your zone when you’re working out complex business problems in discussion with other people, or are you the kind of person who likes testing theories in pursuit of scientific discovery?

This Dream Life Question will give you some insight into the kind of work that you could do (both in your dream life scenario or on your way to it) that you enjoy.

Question 3. What makes difficulty and struggle worth it?

Elizabeth Gilbert, in her book Big Magic, spoke of this idea called the shit sandwich (which she credits to Mark Manson, his article here). The idea is essentially this: 

“Everything sucks, some of the time.”– Mark Manson
“Because if you love and want something enough – whatever it is – then you don’t really mind eating the shit sandwich that comes with it.”– Elizabeth Gilbert

That’s the big truth : that there is nothing on this Earth that is amazing 100% of the time. There are aspects to every job, life vocation and time investment that isn’t incredible, and can just plain suck. So, knowing that, the question you need to ask yourself is what do you love spending your time doing so much, that the negative aspects of it are worth it?

You need to get real with what kind of sacrifices are necessary, and whether that “flavour of shit sandwich” (credits to Mark Manson) is the one that you’d choose above the rest.

Question 4. What have I spent my time doing in the last few years that I felt had little or no benefit to my life overall?

Now I’m not one for regret. I wholeheartedly believe in the cliché that everything happens for a reasonand thateverything can be a lesson if you learn from it. That being said, Einstein did define insanity as doing the same thing over and over again and expecting different results.

It’s okay to recognise when some things aren’t working for you, or if there are things that you wouldn’t feel was worth the investment should the opportunity arose again. You wouldn’t invest in something that you know didn’t work for you in the past. 

Now this question isn’t about reflecting on wasted time. Try and think about the things that maybe made you think, “Hmm, I get why that was necessary/I know that I got some benefit out of that, but I honestly can’t see myself investing more time/money in it in the future.”

Question 5. What am I currently investing my time in that feels forced?

Now I’m not talking about the years spent in school that’s government-mandated (even though I know that many people would argue that it falls into this category). I’m talking about the stuff that you’ve chosen for your life that are part of your life for reasons other than the fact that they get you closer to your goals or because it brings you happiness. 

Do you go to the gym because you honestly enjoy it? Because the pump is a great way to start your day? Or do you go because it feels like what you should be doing?

The fact of the matter is you will only be able to really give your all to the things you want to do.

You need to want to look after yourself to be able to commit to going to the gym. You need to wantto do well at school to motivate yourself to study. 

Identify the things in your life that you’re forcing yourself to invest time into. Now see if you can spin it so that you wantto do it. If you can’t then it may be time to rethink what you’re prioritising.

Question 6. What are some things that I have in my life now that I once dreamed of having?

One of the possible side effects of dreaming big is forgetting to take a minute to appreciate how far you’ve come. 

I’m in the final stretch of my time as a 22-year-old. In the last few weeks I started feeling down about myself and what I thought to be a lack of achievement. But rather than getting stuck in these thoughts, I opened up to a new page in my journal and listed all of the things that I’ve accomplished and all of the wonderful experiences that have stood out to me in the last 5 years.

Those few minutes lifted me out of the beginnings of a quarter life crisis with a renewed pride in myself and sparkling excitement for life as a 23-year-old.

Use this question to reflect on your ‘dream cometrue’ ‘s. The things that once felt so far away. The things that made you think, ‘life would be grand if ……’

Question 7. How does my life now differ from what I see to be my ideal life?

Playing “Spot The Difference” between your life now and your ideal life is the best way to get clear on what needs to change for you to be living your dream life.

It’s one thing to be able to pinpoint what you want your life to look like someday. It’s a whole other thing to be able to identify the path to getting there. 

By positively comparing your life now to the way you dream your life to be, you can draw your map (metaphorically or literally) by working backwards from your ideal life until you’ve reached the point where you are today.

When I first answered this question for myself, I felt like throwing a pity party at how far away my ideal life felt. Allow yourself no more than 3 minutes to feel bad about this. Then go take action towards your ideal life.

Action is the cure.

Take the time to really reflect on these Dream Life Questions. I’ll be completely honest – we can get so much deeper into this kind of self-reflection, but I believe that letting yourself think about these ideas in a general sense can prepare you for some deeper soul-searching. 

I’d love to hear some of your answers to these questions. Or perhaps some of your own Dream Life Questions! Feel free to share them in the comments below.

Sam x

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