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7 Questions to Help You Prepare for a Big Change

Change is hard, but a little self-reflection goes a long way. Learn 7 questions to ask yourself to prepare for a big change.

Ashley Janssen
Ashley Janssen
13 min read
7 Questions to Help You Prepare for a Big Change
Photo by Chris Lawton on Unsplash

Change is a normal part of life but it can feel daunting, overwhelming, and fraught. There are often ingrained patterns of thinking and behaviours that make things harder than they need to be or even prevent you from moving forward.

The following is a self-reflection process that I went through organically as I was preparing for a big change of my own. I found it immensely helpful as I worked through my jumble of emotions, thoughts, and fears.

If you are preparing for a big change in your life, I invite you to take some time to think through these questions to help set a solid foundation for whatever comes next.

My big change

When I decided to focus on writing, coaching, and speaking full-time, it was a significant shift in my life. It was something I had been thinking about for a long time but there were always other priorities. It was something I did on the side for many years because I enjoyed it, but only when I could fit it in. When the opportunity to make this change became apparent, I had a lot of mixed emotions about it.

I knew that I wanted to make this change, that I was going to make this change, but that I needed to calm some of my inner chaos before I could think clearly about the path ahead.

Calm your inner chaos by writing it out

For me, writing everything out is a helpful way to process and organize my thoughts. It forces me to think through what I am feeling, articulate it analytically, and dig deeper into why I am feeling this way.

When thinking about a big change, writing it out is a way to:

  1. Process what it actually means for you, your career, family, or whatever parts of your life it will touch. Big decisions impact many parts of our lives and deserve to be made with careful consideration.
  2. Clarify what is holding you back. Change is hard because it pulls you out of the familiar and into new territory. Think about what you are worried about and what you are afraid of.
  3. Think about where those fears and worries come from. They are often based on old patterns of thinking. For example, if you are someone who experiences impostor syndrome, you may automatically have doubts about your skills and abilities.
  4. Decide what you are going to do about those fears and worries so you can move forward. Change comes with risk because you can’t know the outcome. It is ok to be uncomfortable, it is ok to worry and be afraid. But you have to decide if you are going to let that stop you or if you are willing to push past and accept the risks.

Be as honest with yourself as possible

People tend to soften their language or omit certain things when they know someone else is going to read what they wrote. They want to appear a certain way or are afraid of judgement so they adjust their language.

As I endeavoured to start this exercise, I knew I wanted to be as blunt and honest with myself as possible. I decided to approach it as something that was just for me. There was no expectation that anyone else would read it. There was no need to perform or couch my thoughts.

I encourage you to approach this exercise in the same way, as one that is for your eyes only. One where you can dig deep and say things to yourself that you might not be comfortable with. Things that you might not want others to know about you. Or even just things that you haven’t been able to say out loud yet.

Be honest, not critical

This isn’t about being critical or tearing yourself down but rather reflecting on different aspects of yourself from different angles with as much honesty as you can bear. There will likely be a mix of positive and negative things, as well as things that are neither positive nor negative, things that are simply part of you.

You may choose to share this reflection with someone you trust later, but you don’t have to. You can keep it just for you, or delete it, or whatever you want. The important part is going through the process itself.

7 questions to help you prepare for a big change

These were the 7 questions I came up with when I was working through this self-reflection. They might not be the right questions for whatever change you are about to embark on, but they will give you a starting point.

1. What do I know about myself?

This question is meant to set a baseline. For me, some of that baseline is behaviours or ways of thinking that I know I engage in that have been limiting in the past. Some of it is expertise or skills that I know I have that are important to part of my change.

For example, one of the things I identified as limiting for me is that I feel uncomfortable with self-promotion. I know this comes from a combination of fear of judgement, as well as wanting to be liked. I also know self-promotion requires that you accept that you will be judged, and there will be people who don’t like what you are doing or saying. I will have to promote myself to reach people and be a successful writer, coach, and speaker.

On the flip side, I know I am a good coach. I know because of the feedback I get from my existing clients, what I can see for myself during the sessions, and as well as over time as I witness the changes my clients make to their businesses and lives. I also know I love coaching. It is something that energizes me and brings me joy, it is what made me want to make this change in the first place.

When you think about what you know about yourself, ask yourself questions like:

  • What makes me uncomfortable?
  • What energizes me?
  • What types of situations do I often avoid?
  • How do I respond to stressful situations?
  • What do I know about my expertise and skills?
  • What is difficult for me?
  • What do I know I am good at?

2. What am I proud of?

This question pushes further into the things you know you are good at. The things you are proud of are the foundation of your life. They are what you have already put significant time, energy, and attention into. They are the things that were challenging that you overcame, or the relationships you forged, or the skills you practiced and developed. They are at the core of your ‘why’.

One of the things that I listed that I am proud of is my fitness streak. I have worked out every single day since January 1, 2018. I have done yoga, outdoor running, HIIT, strength training, or pilates, every day for 20-45 minutes. While it was important before, my health became even more important to me after my multiple sclerosis diagnosis (which was about 8 weeks before). The MS started as the motivator, but it is only one of many now, and I am proud to be in the best shape of my life.

Identifying what you are proud of can be rough since it requires self-praise. Remember that this is for you. You don’t need to make yourself seem smaller or think about someone else’s feelings or be humble. This is an opportunity to crow. Hell yeah, you get to be proud of yourself!

Big or small, think about the different things you are proud of like:

  • People and relationships. Your family and friends. All the people you have added, or the people you have let go.
  • Career path. It might have been a direct line, or (more likely) a winding path. It might be based on something you went to school for, or perhaps has nothing to do with school. It might be something you never thought you would do or something you always wanted to do.
  • Physical health journey. Team sports, fitness, body acceptance, sickness, injuries. There is a wide variety that might apply.
  • Mental health journey. Going to therapy, taking medication, cultivating self-awareness, working through past trauma, meditation. This is another wide gamut of things to be proud of.
  • Hobbies, skills, or areas of expertise. This could be anything, like an instrument, programming, learning a new language, crocheting, baking, gardening, etc.
  • Community and volunteering. People and causes you are passionate about that you have invested your time and energy into growing or cultivating.

3. What are my fears and worries?

This one is a doozy. It’s a loaded question, often tied to identity-level thought patterns with some variation of, “I am not (good, smart, qualified, etc.) enough”, or any number of self-defeating thoughts. They are normal, but they need further examination because they are also not true.

Layered into these thought patterns are the worries like, “what if I fail”, “what will ‘people’ think?”, “what if that idea doesn’t work?”, or “what if I don’t make any money?”.

Instead of asking these questions into the ether, you need to think through the actual answers (as far as you can answer them). These are the starting points of mitigating the risks of these worries, finding solutions, or at least acknowledging and moving past them.

As you think about your fears and worries, try to get past the first blush of whatever has been whirling around in your head. Ask yourself:

  • Why does this matter to me?
  • What specifically about the change I am about to make am I worried about?
  • What thoughts are holding me back?
  • What am I afraid could happen if I go ahead with this change?
  • When I think about what I am afraid of, where might the fear be coming from?

One of the things that I listed as one of my worries for this shift in my career was that it was selfish. I have 2 other businesses with my partners, Dana and Matt, and I don’t want to let them down. Though Code and Effect and Tadum are doing great, this change does have a real impact on them.

Instead of just worrying about it though, I wrote it out and realized that I needed to have an actual conversation with Dana and Matt to find out what THEY thought. Turns out they were both excited and happy to support this new opportunity (and revenue stream) and together we made a plan to shift my responsibilities around to make it happen.

4. What does failure mean to me?

Failure is a big, encompassing word. It can mean many things, but once articulated, it becomes smaller. It’s easier to hold in your mind and make the decision about what’s next. Either you’re willing to accept the risk of whatever that failure means to you and move past it, or you’re not.

No one wants to fail, but it’s easy to forget that failure (or mistakes, or missteps, or things going wrong, or not the way you planned) is inevitable. It’s going to happen, in one form or another. Full stop. Instead of letting it paralyze you or stop you, take the time to analyze the true risks, and plan for them. Catastrophizing and imagining what failure would look like is actually a good way to come to terms with it.

Ask yourself, if you failed:

  • What is the worst-case scenario of this life change or decision?
  • What do I stand to lose? Am I ok with that risk?
  • What are the resources I would spend?
  • How could it impact my family? Can I protect them?
  • How could it impact my reputation? Do I care?
  • What are the real consequences?
  • What could I do if the worst-case scenario happened?

Around the time I was working on this, I happened to be listening to the audiobook, Born a Sin: Stories From a South African Childhood, by Trevor Noah. A quote from it that stuck with me is:

Regret is the thing we should fear most. Failure is an answer. Rejection is an answer. Regret is an eternal question you will never have the answer to...and it will haunt you for the rest of your days.

As I worked through what failure meant to me, (no one subscribes to Every Intention, no coaching clients, no one interested in my speaking), thinking about failure and regret in this way helped me a lot.

I don’t want to regret anything. Do you?

5. What does success mean to me?

The answer to this is SO important, perhaps the most important of all. One of the biggest challenges entrepreneurs face is the constant bombardment of external measures of success. How many TV shows are committed to following the lives of the rich and famous? How many TV shows unrealistically portray someone’s success as “one big moment” (house flipping, America’s Got Talent, Shark’s Tank, etc.)?

Part of hustle culture is defining success from a strictly financial perspective. It’s very focused on a bigger, faster, louder approach. This is not a wrong approach by any means. Wanting to make money is absolutely one of the goals of building a business. But there is so much more, and you need to take the time to clarify what that “more” is for you.

The answer to this question comes down to understanding what motivates you, which could include:

  • accolades
  • financial wealth
  • a big house
  • nice car
  • vacations
  • living in a particular neighbourhood or city
  • impact
  • reach
  • internal satisfaction
  • the joy of the work itself
  • stability
  • flexibility
  • ...or any combination of these and more.

There is no right or wrong answer. These are all valid and reasonable. You just have to know that you are working towards what YOU want, not what you think you SHOULD want or what someone else has defined for you.

One of the exercises my mentors have encouraged me to go through many times in my career is to think about what I imagine my business to look like in 5 years. This helps create a vision that you can pull from as you gain more clarity. Ask yourself, in 5 years:

  • What do you imagine yourself doing in your day-to-day?
  • What are the things you want others to say about you?
  • Who are you working with?
  • What impact have you had?
  • Who have you surrounded yourself with?
  • Where are you living or working?
  • What is your lifestyle like?

At the end of the day, if you don’t know what you are working for, what you are working towards, then what’s the point?

My fav quote on this is from Lewis Carrol’s, Alice in Wonderland:

Time will pass no matter what you do. If you are clear on what success means to you, you can then be intentional about how you spend that time and the steps you take to achieve that success.

6. Who do I want to strive to be?

I included this question as a way to think about a version of my future self that I want to work toward. Beyond articulating what success means, this is asking what internal identity shifts are happening, or will happen, as I make this change.

For example, early in my entrepreneurial career, it took a long time for me to internalize and feel comfortable referring to myself as an entrepreneur. My impostor syndrome was very loud and identifying as an entrepreneur felt like a lie. Some of this also came from not connecting with what I thought it meant to be an entrepreneur. Over time, I came to realize that there are many ways to look like and be an entrepreneur, and one of those ways looks a lot like me.

The language we use to describe ourselves is important. The words we use and identify with will frame how we understand how we fit in the world.

Think about the words you use to describe yourself today. Are they the same words you want to be able to use in the future? Do you identify as a writer, gamer, parent, creator, artist, partner, runner, programmer, musician, connector, entrepreneur...or any of a million other descriptors?

Significant life changes often coincide with identity shifts. Ask yourself, in the future:

  • What are the words I want to use to describe myself?
  • What are the things that I know about myself today that I hope will be different in the future?
  • What are the things that I know about myself today that I hope will be the same in the future?

Try finishing the sentence,”I want to be someone who ______________.”

7. What do I need to remember every damn day?

As I worked through each of these questions, things came up that turned into a list of affirmations. They are the counterpoints to my fears and worries. They are the words of support I had heard from others. They are the things I teach my coaching clients that I try to practice myself. They are the reminders that help me acknowledge the parts of myself that sometimes hold me back. They help me move towards my goals, and the successes I have defined for myself. But it’s hard to keep these thoughts at the top of my mind.

What do you need to remember EVERY DAMN DAY to help you get through it and move forward towards your success?

Make your change

When I did this self-reflection exercise, I wrote for nearly 3 hours, stopping only to get more coffee. I wrote 5 pages, point form, pouring my heart out in a way I hadn’t done in a long time. I bounced around between sections as different reflections brought up new thoughts. I even had a few times where I felt a little emotional.

When I was finished I felt a huge weight lift off of me. The fears and worries were not suddenly gone, but they were smaller and more balanced with excitement and positivity. I could clearly articulate what failure meant to me, and accept those risks. I was able to look forward and imagine what success looked like and feel motivated to achieve it. I reflected on the parts of myself that I am proud of, and the parts that I am working on, and know that all of it was ok. They are what make me, me. I know who I am today, and at least some of who I want to become.

And I made my big change. :)

You might work on this in one fell swoop like I did, or take a crack at each section over a few days or weeks. The questions you ask yourself might be different from these. There is no right or wrong way to do this.

The answers to these questions will change over time. Sometimes the fears and worries will balloon and feel overwhelming again. Your definition of success might shift slightly or change entirely. You will gain more things to be proud of. Your vision of your future self will evolve.

What’s important is that you take the time to get clarity on these different facets of yourself. Set your foundation and make your big change with confidence. If you decide to give it a try, I would love to hear about your experience.


Are you thinking about making a big change in your life? Do you want some help to work through this process? Schedule a free consultation!

IntentionResilienceStrategy
Ashley Janssen

Ashley Janssen

Writer, business coach, speaker, entrepreneur, chaos calmer, introvert, cat-lady. Lover of books, fitness, old fashioned’s, basketball, and video games.

Follow me on Instagram, Twitter, and LinkedIn.


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