the top 10 ask me anything life & business questions & answers


Top10AskMeAnythingAfter last week’s Ask Me Anything Day, several people asked me to share the questions and answers that other people were sending and receiving.

So today I’m sharing the “Top 10” of the questions from this Ask Me Anything roundup.

Obviously, each exact question was only presented once, but they represent a host of other questions along the same lines.

And remember: the challenge was to ask and reply within three sentences or less (which I stuck to as much as possible).

Let’s take a look at the top 10, shall we?


The Top 5 Life Questions


#5: How can I exfoliate a friendship?

Have you ever had to exfoliate/makeunder a friendship?

How did you know? How did you do it?


Yes, I’ve had to do that before, most notably in college with a group of friends who were more negative than I liked. It was really tough, but I slowly just stopped hanging out with them and found ways to not be around them.

At first they didn’t like it, but over time they realized I wasn’t going to be around and they stopped asking. I also did this with a group in Chicago. Again, I happened to be busy most times they wanted to hang out.

But if it was a close friendship that warranted more explanation, I’d be honest and share what I needed to do for myself (vs. criticizing them).

But remember: you cannot control how they will react… just share with love, honesty, and kindness what you need.


#4: How do I create intention-based routines?

How do you set up and follow through with routines that are in line with your intentions?


Great question! I remove things in my life that take up the time/money/attention/or other resources necessary to make room for my Value-led actions.

Linchpin habits are particularly helpful. Also, overcoming resistance is a big part of it, too.

(Note: I cover this extensively in the  Life With Intention Process.)


#3: How can I overcome shyness and doubt when making friends?

I often am shy/withdrawn in some social situations especially with new people.

I think it is a confidence thing– I often feel like “why would these people want to hang out with me” or “why would this attractive, funny guy like a girl like me?”

As a result, I don’t become friends with these people– how can I overcome this? 


With all my love here is my suggestion: stop thinking so much about yourself and what they think of you — start thinking more about them.

Be there to reflect and appreciate their awesomeness in conversation. Ask questions, get curious, and reflect the wonderfulness that is inside you both.

“People may forget what you said, but they never forget how you made them feel.” – Maya Angelou


#2: How do I find life purpose & meaning?

I am having a hard time finding direction, meaning, purpose in my life right now.

I somehow lost focus, drive and energy even to do my tasks at work. I feel I am chasing time…life… so many things to do and yet I am on a stand still. Please advise. 


Great question, Hun! Thank you for sharing.

I’d spend time trying this writing exercise to get clearer on what is going on in your life and mind.

And I’d also spend time thinking about and defining the Values you have for each area of your life. Then, I’d read The Slight Edge and The Seven Habits. : )

Note: Here’s my take on “life purpose.”


#1: What should I do when I doubt my gut?

After your last AMA, you posted about many readers feeling lost and the importance of listening to your gut.

The thing I struggle with is doubt, even after I’ve made the decision.

Do you also struggle with doubt, and if so, how do you move past it?


Great question, Hun! I think our ego will always have fear about anything unknown. And our gut will often tell us to do something with an unknown outcome.

So the point is just to see the doubt, and take action from the gut anyways. 

I know this isn’t fancy or amazing, but our ego will always doubt. The point is to never let it stop us from taking action.

And the good news is that as we take action, we get more used to doubt, but also more used to acting anyways.



The Top 5 Biz + Career Questions


#5: How do I quit my day job and go full-time with my business?

I work full time currently and freelance a LOT on the side, but am dying to quit my job and just do my design freelance full time.

Any advice or recommendations?


Yes! I’d listen to Kim’s podcast episode – specifically where she shares how she transitioned from her day-job to full-time. I think it will be really helpful – just find your “spaghetti number” and work towards it!


#4:  How should I create a website with a limited budget?

If I have a small budget, is it worth hiring a professional web designer – and at what cost?

What’s the most important thing to keep in mind when developing a vision for and maintaining a website ?


Great question! You can do anything, there is no “right” answer here.

But my personal suggestion is to find someone to design a nice logo you like, and then find a great looking site template (check out places like and use the two together to start.


#3: What business programs do you recommend?

What business training or programs have you done that you highly recommend to take one’s online biz to the next level?

Specifically, in getting clarity about what to offer, how to reach the right people and creating content that matters.


Great question! To be honest, I started my first biz at 15 (almost 15 years ago now) and never did a training program besides a business degree at the University of Michigan Ross School of Business (that didn’t really apply to my business specifically) – I learned from trial and error over 15 years.

But I would highly recommend listening to The Smart Passive Income and Ask Pat podcasts to get great advice on business at all levels.


#2: How can I be confident about the decisions I’m making in my job (or business)?

I recently (in the past 4 months) took a big step up in my career, with full backing and support from the company, but I’m struggling a little with the confidence to take the decisions needed/trust myself to be giving the right answer.

How do I get past myself? Any advice or resources will be so helpful!


Great question, Hun!!

I’d try doing this writing exercise when you find your ego is clouding your judgement about… anything.

It might seem strange to do this for a professional decision vs. a personal one, but the process really helps you get out of your head and stop rationalizing. : )



I want to change my career path, but am uncertain of exactly what I’m meant to pursue, even though I’ve been working to figure it out through reading books, listening to podcasts (like yours!), journaling, mind-mapping, meditating and the like.

I have a strong list of my values, but can’t quite put my finger on how they work together to create a career I’m passionate about.

Any advice on how to discover this and make the leap into a life with real intention?


First, write to your gut to find out what is going on – why the confusion? Why the cloudiness? (Seriously, please try this!)

Then, while writing to your gut, consider:

Who do you want to serve in this next chapter, and how do you want to serve them? 

This isn’t about “forever” it is about your next chapter.

You don’t need a 10 year plan… you need to know what your gut tells you is the next right move.


The Biggest Takeaway


Overall, what I noticed from this round of AMA, as well as the previous round six months ago, is that many questions about HUGE life choices or business topics required one simple and universal response:

The answer you are seeking is within yourself. 
Uncover what your intuition wants you to do right NOW, and then go do it.

For each of these intuition responses, I shared an easy, quick, and insightful exercise called writing to your gut to help you do just that.

If that sounds weird, please go over and take a look at my own gut conversation that I’ve shared to get a feel for how powerful it can really be.

After seeing the exercise in action, many people are inspired to try it themselves.

I hope you do, too.  


With all my love,


PS – Life With Intention Online registration is opening next week!

(If you want to get more details and special bonuses, hop on this exclusive list.)


This Post Has 8 Comments

  1. Thank you so much for posting these! I’m in exactly the same position as the person who asked about being more confident at work so I’m going to try that asking questions technique. (actually I’d love to hear about the person who emailed you gets on with it too, if he/she feels like sending an update at some point..)

    1. That’s great to hear! I hope that approach helps you. Sometimes in order to get over our own hurdles we need to take our attention off ourselves and onto something else, or in this case, someone else. Not to let our own self doubts get in the way of connecting and sharing with someone and learning about someone – by being more interested in them than how they are thinking about us, we can overcome our ego’s second guessing. You know? Something to at least practice and experiment with. : )

      If that reader responds with an update I’ll ask her to share it here, too!

  2. Carmel David

    Great post! Love what you said about the answer being within ourselves. Reminds me of a quote by Viktor Frankl, as mentioned by Covey in 7 Habits: “We don’t invent our mission, we detect it. It is within us waiting to be realized.” 🙂

    By the way, are they any changes to your LWIO classes? Do you have upcoming refresher courses or something? Thanks!

    1. Exactly! I think that quote sums it up very nicely. : )

      As for the class, it is now going to be expanded and 6 weeks long with modules, private community forum/site, and the whole 9 yards! Alumni of the class from this winter will get access to the new format as well when we kick off with the next class this month. All details will be shared next Tuesday!

  3. Jess, I loved reading all of these questions and responses and want to go back and read some of your resources. Do you have a post or guide somewhere on determining if something is your ego or your gut telling you to do or not do something?

  4. Kristina

    Jess, I didn’t submit a question myself because my head is so full of questions that I just couldn’t find one to ask within three sentence. However this little roundup you shared did answer a couple of my own questions and especially “the biggest takeaway” is a great reminder! Thank you for sharing! I am also so so excited for the Life With Intention Online and can’t wait to register next week.

    1. That’s awesome to hear, Kristina! I’m glad these answers helped, and especially that last part!

      I can’t wait to have you in class, Hun!

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