Real Talk

How & why to do a self-assessment of your life.

Doing reviews like this always remind me of how sports coaches have to watch (and study!) game replay tapes. Like video replays, data doesn’t lie. The important part here is that you look at what happened without bias or judgement; simply identify the facts for what they are. This can be challenging though because a lot of the time your perception and memory doesn’t always match up perfectly with reality.

It’s important to reflect on what happened – regardless of the outcome, what you’ve accomplished, achieved, etc. – in order to evaluate WHERE you’re coming from and how you get to wherever HERE is at the moment.

If you feel you’ve been making progress- that’s great and you should be proud of that. Celebrate that. Just remember, it’s not over – there’s always something to learn and improve upon. THAT’S what is going to really put you on the fast track. Plus, you want to make sure you’re attributing your success to the right drivers. And I think figuring this out is often what separates being good from being great.

When we thoughtfully study the past, we find clarity. And with clarity, you can gather insights to guide your decision-making process for what to do in the future – what to change, what to focus less on, etc.

Now that you have an idea of how and why I came to my own self-assessment, I’ll guide you through how to do your own! I hope your excited, because I am (clearly!!!).

Conducting a Self-Assessment: Why Should You Do One?

We all have our areas of improvement, and usually that happens in the form of goals and resolutions – which is great and all, but it’s pretty hard to make a goal and expect to make changes without understanding WHY you want those changes and HOW you work as an individual. If you’ve been hanging around for a while now, you know that resolutions aren’t really my thing (click here to find out why) but, it is for some of you so I’ll use the word and move on. So essentially, doing a full self-assessment brings you to the core of your goals and who you are as a person – and how you operate. It’s grounding you and your goals and turning them into something concrete that you’ll actually be able to obtain. Plus, it’s honestly incredibly refreshing to really feel in touch with yourself. It’s a way to open up your soul and brain and get to know yourself a bit more. Seriously, it’s cool!

How & where do I even begin?

There are probably a million ways to conduct a self-assessment, and to be honest, mine looked like tons of scribbles in a notebook that were eventually compiled onto a different notebook. And then recompiled onto Evernote etc. etc. But I wanted to put something together to GUIDE you through YOURS.

The thing about self-reflection is we probably all want to do it (because it sounds amazing, duh), but knowing HOW to do it is the hard part – at least it was for me. Before we can even look at the data and view our tendencies, we have to first come up with that data. Keep scrolling.

Self-Assessment walk through questions

Personal – Successes

  1. Personal accomplishment that made you feel the best?
  2. What aspect of it made it feel so good?
  3. Did you do it for yourself or others? Was it attached to a moral?
  4. Did you feel completely satisfied with it when it was over?

List 5 other accomplishments over the last year and follow suite with the questions to get to the bottom of why these PERSONAL accomplishments meant to so much or had a lasting positive affect. Consider areas of your life such as health, fitness, emotions, spirituality, fun, travel, lifestyle etc.

Personal – Failures

  1. List 3-5 personal experiences that made you feel the worst. Then consider, what aspect of them made it FEEL so bad.
  2. Were these experiences/failures things you could have controlled? If so, have you identified any lessons you can learn from the experiences? List what you learned for each and how you can implement or take action on it to improve your experience next time.
  3. Think about WHY these experiences affected you so much? Consider how the experience is influenced by your personal values, desires, and expectations of life.

Personal – Growth

  1. What’s a dream or desire of yours that you have yet to accomplish? Or what do you fantasize about when you think of a “better” version of yourself? What do you feel like is missing from your life? If you had to imagine your BEST self, what would she/he look like? How would he/she spend her/his time? Do your actions reflect these beliefs in your own life?
  2. What’s something that you constantly think about improving but don’t? Why? What could you start doing today to get closer to whatever it is? What could you eliminate? What’s your bucket list? Can you do something to cross one of those things off in 2018? Can you start planning for it right now? Why are the items important to you? Are you doing them for yourself or others? Or because they seem like they should be on your bucket list?
  3. What are my STRENGTHS? Consider all aspects of your life and personal characteristics such as follow through, tenacity, social skills, communication skills, thoughtfulness, compassion, patience, enthusiasm, creativity, trustworthiness, honesty, engaging, dedication, analytical, curious, etc.
  4. What are my WEAKNESSES? What are my biggest distractions from being my best self? Consider things like your focus, commitment, fear of missing out, listening skills, follow through, ability to balance multiple pressures, response to pressure, procrastination, articulation, communication and interpersonal skills, confrontation, admitting fault, etc.


  1. What aspect of your job do you like? What about your job do you find most satisfying? What excites you about it? What makes you feel productive and like you’re getting a lot done?
  2. What aspect(s) of your job do you dislike the most? Specifically, what tasks do you not like doing? (List 3-5 things you can’t stand doing or that lead to procrastination). Can you delegate those or move them closer to something you like doing (by changing how they’re done or the experience you have when doing them?)
  3. What is the culture, value system, and mission statement of your current company/employer? Does your personality match up with the tasks and culture of the company? Why or why not?
  4. Do you feel empowered in your job? Why or why not? Do you see how the work you do makes a difference to the success of the company? Do you feel passionate about making that difference? Why or why not?
  5. List any specific accomplishments or positive feedback you’ve received over the past year. Review emails, projects, memos, or your calendar to trigger your memory – I suggest going through each month and breaking it down by project or milestone. Which strengths of yours attributed to those #wins? What makes you different than others on your team or in your office (or in your industry)? How can you better focus on your strengths?
  6. What are your biggest struggles at work? In other words, which tasks to you feel take you longer and feel less productive? Is there a way to delegate or shift responsibility so you can focus on your strengths? It’s much more productive to do what you’re good at (and spend more time doing that) than try to FORCE or FIX your weaknesses. We all bring something different to the table.


  1. Name the people in your life that you enjoy seeing (and rarely cancel on):
  2. Name the people in your life that you don’t feel your best around (or usually want to cancel on):
  3. Why are you still hanging out with people from the above question? It’s likely out of guilt, loyalty, or worries that they’re cool or that they give value to some ego part of your life – when they likely don’t. What would happen if you cut them from your life? Is it so bad? Why aren’t you hanging out with the people from the first question more? How can you prioritize them better into your schedule? Make a commitment to doing so and be specific about when you will do it, come up with ideas for WHAT you’ll do together and how you can spend more time with them.
  4. Who in your life do you respect the most? What aspects do you respect? How can you pick up some of those aspects in your own life?


  1. How do you feel about your current financial situation? Overwhelmed? Confident? Consider your overall income and lifestyle expenses in relation to your spending, budgeting, and saving for short and long term.
  2. CONSIDER YOUR INCOME- this will depend on whether you’re an employee or an entrepreneur, but reflect on how your income affects your lifestyle and/or whether you feel like it’s holding you back.
  3. CONSIDER SHORT & LONG-TERM SAVINGS – Contributing to your short and long term savings is usually closely tied to your commitment to budgeting or consistently setting money aside. List the things you ARE saving for and those you want to START saving for. Consider retirement, home ownership, personal investments, taxes, travel & vacation, gifts for others, accidents and unexpected expenses, etc.
  4. GIVING – I’ve found that I am much better at giving when I PLAN for it. Considering your income and personal expenses, figure out how much you’re willing and wanting to save if it’s important to you, make sure you set up a system to make it happen.
  5. What are you most stressed about? (List 3-5 major financial stresses right now). What can you do each week to make your financial situation more confident?
  6. What on your bank statement can you remove from your life?

Now, you could open this up to other themes – depending on what your life looks like or anything you want to focus on (kids, health, business, whatever), but essentially the reflection stays the same. You’re trying to get to the bottom of a few things and then collect data based on those areas.
To be honest, I spent WAY too much time on this blog post and even as I’m hitting publish, there’s actually so many ways I know I could make it better. BUT I hope that as it stands, you’re still able to find it beneficial and at least use it as a guideline! If you do end up using it or reflecting by way of these questions PLEASE let me know! Either via comments on Instagram or by commenting on this blog post!

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