Category: Outside of the Lines

A Manifesto For When It’s Not OK


Do not pretend.


If you want something, stop pretending that you don’t.


If you don’t want something, stop pretending that you do.


If you are settling or stalling or stuck all together, stop pretending that you aren’t.


I know the game, I played it well. Pretend.


Today I am answering a question from a fellow Barefoot Boardroom Member who responded to my email from last week and wrote:


“Kelsey, I loved your video today, you hit me right between the eyes.


Here’s the problem though, deep down even though I know there is more for me, more to me and even a part of me I never show, I feel like I have all of these dreams and ideas that I never get to because I am stuck pretending to be OK.


How can I do something about it when I spend most days convincing myself everything is OK?”


I recorded a little video where I share two things I spent too much time pretending about and my process for identifying, discovering and breaking the cycle of pretending or settling for just OK.

Watch the VIDEO Here (CLICK)

Connect with me and other Barefooters in the comments below (like way below….keep scrolling). Come share where you have been a pretender, what you have done to break through the ‘OK’ barrier. I’m interested to discover where we find common places to pretend that everything is OK, and where it is not.


I think we all have times and places in our lives & career where convincing ourselves that everything is OK can hold us back from getting what we really want.


Reality does not like pretend.


If we stop pretending we can find time to create a new reality.

The one we truly want. – Kelsey Ramsden


Most people who have never had businesses of their own think that owning a business automatically means you have dough.

“Sure, you can get the check because you can just write if off.”


Do these people understand that having a business is the most delicate balancing act of cash management that anyone can likely undertake? That the cash we all have is as precious as air itself and that writing things off does not mean free money?

When I was at MBA school all of these professors would say ‘cash is king’ as religiously as I tell my children to wash their hands…..consistently and with purpose.

I was paying attention at school but never really understood the seriousness of this message until cash in my first business became more than king….it became air….without it we were going to die.

I remember going in to my amazing accountant and saying “This year end looks awesome! We made some good money, eh? But, where is all the cash?”. She replied “Well, those financial statements who what we did but there is no cash, and actually we need $600,000 by Friday.”

WTF was an understatement.

I knew how to read financial statements and my MBA brain got too caught up in what they read to be paying attention to the cash…..and truthfully I knew the cash was running out and I was kind of avoiding asking the question because I did not want to address it. Ignorance is bliss – or so they say. Until ignorance takes the shape of a six figure number and then ignorance made me sick to my stomach and run for the closest waste paper basket.

Cash is king.

Cash can also be air.

So, here is what I know from learning things the hard way:

  1. Always, always, always know how much cash you have in your account.
  2. Take that cash in your account number and subtract all of the payments you have in the mail. That is cash or cheques which are in envelopes travelling to their rightful owners by way of a lovely post man or mistress.
  3. Figure out your ‘burn rate’ – this is how much money it costs you to keep your business running a month. Keep this number as close to low as you can. Map out your expenses on a calendar.
  4. Never assume you are going to get paid when you think you will – add at least a two week buffer for receipt of earned revenue.
  5. Invest interest free when you can in building your business. Try and grow organically when possible.
  6. If you must leverage (borrow), work with a lender where you can speak face to face with the decision maker on your file. You might need to rely on a good relationship one day.
  7. Ask for terms on everything. Stretch your money out to build your business, hold on to it for as long as you can.
  8. Ask for pre-payment and retainers whenever you can. Use client money to build your business.
  9. Balance Sheets (B/S) stand for ‘bull sh*t’ when you are in a cash crunch. Income statements (I/S) are called ‘imaginary statistics’ when the cash runs out. Stop listening to your financial statements alone to measure your business health – look to your cash as well and often.
  10. Cash is like a tide – it goes out and in and out and in… not panic when it is out, but understand well how and when it is coming back in and always be conservative. It might be a full moon kind of month when forces outside of your control keep the flow out for longer than usual.

Tweet it:
Balance Sheets (B/S) stand for ‘bull sh*t’ & Income statements (I/S) are called ‘imaginary statistics’ when the cash runs out @kelseyramsden

I am working on structure for the financial secrets component of my course right now, so I could not help but share a few of my tips with you now, before the course launches in September.

Cash is something we seldom talk about because it is so personal and a topic so close to the heart  of almost every entrepreneur who knows all too well the feeling that overcomes when you are short on cash…..I would never wish this feeling on anyone. Well, there is this one guy…but aside from him, no one (I’ll tell you that story another time when I talk about partnerships).

The truth is that when we are worried about the cash position of our business we are not working on our business – we are distracted and acting from a place of lacking and fear and this is never, ever good.

It is true that when I am in the flow of my work, my business and what I do to add value to people’s lives or my business, then the cash flows too. When I am in fear and forced ignorance, nothing works nearly as well and the flow stops altogether.

So, if you are ignoring your finances – this is permission to be fearful and not want to do something about it but to pull up your socks and get to the truth of it. Trust me, you and your business will be better for it no matter what you find.

With trust and truth,

PS- I want to take this amazing opportunity to welcome some new countries to my readership….growing like a wild weed and loving it…..welcome to those of you in Portugal and Qatar! So happy to have you along with us for the adventure of life and business together. Keep the share fest going….spread my love and insights amongst your friends who have or want to start businesses that support them in the amazing life they want to have.

with love…… xo

Like most funeral talk, I prefer to keep it short.

So, this post will be potent and petit.

I almost died once.

One time that I know of….I think we all narrowly escape death many times without ever knowing it but this time I had a high probability of death and I knew it. It was cancer, rare, deadly and does not respond to chemo or radiation…it was up to the knife.

I was scared.

Scared is a coward way of saying I rocked on my kitchen floor sobbing.

Because I am a bit of a controller when it comes to planning parties and creating atmospheres and memories, it occurred to me that I ought to put some thought into my funeral and plan it all out so that it would be exactly as I wanted it and no one could go picking some song I hate or serving potato salad (also hate).

I made a list of five songs to be played at the funeral.  I won’t share them because it will ruin the surprise.

I made a list of the desserts I would like served at the reception after. A mix of family traditional squares, cookies and tarts.

Then, I decided that I ought to write my own obituary/eulogy. Odds are that those closest to me will be too emotional to come up with something magic within those first 48 hours or so after I died….so I might as well draft the words that the last thoughts of me would float away on.

Out of respect for my family an so as not to ruin what might be one of the best pieces of writing I have ever done I will only reference singular words which appear in the text…..but it should be enough for our purposes here today:

Tender Mother
…and the list goes on.

After I wrote out how I wanted to be remembered I reflected on how much like ‘me’ those paragraphs of prose were. Is this the person I am living out my life as today? Is this really who I am….or could it be that this is the person I want to be? Do the people who know me best see these things in me….do I show them?

Another drop me to the floor moment.

We are all dying. It is just the pace at which we are going that differs.

So what is it that you want to be remembered as? Who are you and are you living it, showing it? What would be said at the celebration of your life if it were to happen this weekend? What about if it were in 1 year, 15, 45?

It occurred to me that living by my eulogy….with each decision and moment, living up to that which will be printed as my obituary – this is the life I choose, I desire, I shall live.

What would life be like if we lived our eulogy every day. If we were that person and let it show at all times? @kelseyramsden

I share this with you because it is intimate and scary and vulnerable and true and because we don’t all get a chance to live through near dying soon enough to see the opportunity that presented itself to me……to live my obituary every day.

I also share it for totally selfish reasons shrouded in a gift for a friend. I am going to forward this post to my best friend and ask her to write her eulogy for me. I will be of no mind to do it if ever she were to leave this fine earth before me and it would be great to have it pre-arranged….and because I want to pass along the gift that living ones obituary can give.

Although this is a downright inner-circle of trust post to you, I give you full and free right to forward this on to your best friend, brother, sister….whomever. It’s not really about me in the end….it is about you and the people you love…and the life you have been given to live….and how you want to live it.

In the spirit of living out each day as if our eulogy were being written upon it…..

PS- A tremendous thank you for the overwhelming outpouring of help from my post asking for interviewees. Our phones and inboxes were overcome with a tidal wave of people wanting to share your stories and ideas and experiences. I am just so thankful for the amazing group of people I get to share my insights with each week and for what is going to be an epic three weeks of interviews.

When was the last time you considered this question: Is this my life?

Well, is this YOUR life?

The life you wanted to live when you were 20 and looking forward at your career with open anticipation for what the world might have in store?

It probably is not, and in all honesty I hope it is not the life you imagined when you were 20 because you likely did not have enough life experience yet to know what it is that you really wanted.

Perhaps you knew you wanted a child and a white car and a husband that brought you flowers but did you know the kind of environment you wanted to be surrounded by at work or the kind of best friend you would need in times of turmoil or even the point at which you draw the line on giving and taking?

Odds are that in your deepest heart of hearts you now know a lot of these things. The hard truth is that many of the things we come to know about ourselves are never acted upon.

We start out in our careers when we don’t yet ‘know’ – chart a course from there and then, despite changing seas and signs, neglect to check or re-correct the course. So, when we land on the distant shore of our career, we find we are not where we want to be.

Is your career as you want it?

As Canada’s #1 Female entrepreneur two years in a row you might assume that my angle on this one is to try and convert you to quit your job and start your own business. Your assumption is only half correct….here’s why.

A number of us in careers want to stay in our careers and just need to make some changes to move toward our ideal place in the sun. The rest of us do need to quit. Which group are you in?

Answer these 10 questions to find out:

  1. Have you ever felt that you had something unique to offer the world which you have not shared with them yet?
  2. Do you feel that your truest self can show up for work each day?
  3. When you leave work each day, do you feel that you are one step closer to a personal goal?
  4. When you think of your life 10 years from now, are you positioned in the right place today to be able to get there?
  5. Are you surrounded by people who challenge and inspire you in your career?
  6. If you sat beside a stranger t a dinner party who turned out to be in the same line of work as you are, would you talk work all night or switch seats?
  7. If time travel were possible and your future self met you at the breakfast table tomorrow morning, what career advice would she give you?
  8. Do you know how much money you need versus how much you want – would knowing that information change what you do for work now or looking forward?
  9. Does your career define you and are you happy with that definition?
  10. If the emotion of fear were stripped from you, what are the top three things about your current career you would change?

If you answered the above 10 questions very honestly I applaud you! It can be scary taking a true account of our lives. Sometimes letting sleeping dogs lie is an easier path, unless of course the dog is going to wake up very upset that you let it sleep through it’s best opportunity to live out a great remainder of its life.

I am often told by clients and those who approach me after I deliver a talk that they just want to feel happy. That they feel dissatisfied and like they are not living the full life they want to live.

You see, one of the key elements of happiness is knowing deeply and truly that you are where you want to be or at the very least, that you are taking action to move toward that feeling.

One of my favorite quotes goes something like this: If you want something you have never had, you are going to have to do something you have never done in order to get it.

For many of us, the thought of change sounds like risk…..the idea of something different brings up the possibility of failure more than it does the possibility of success…..this is why so few of us wake up one fine day and begin to move toward our ideal career or life. It is the possibility of not achieving what we set out to do that keeps is stagnant. Illogically we stay unhappy for fear of being unhappy.

I wanted to write this article and share if with you because I have found myself entering a new era of life over the past two years and for this new era I am so very grateful. I never would have become my fulfilled self in mind and body if it were not for having asked myself the above 10 questions. More than anything, I hope that you take he time for yourself to take a look at where you are at ever now and then and choose to adjust your course for where you want to be, who you want to be, your truest self whom is deeply fulfilled and happy.

Isn’t that what we all want after all?

In the spirit of possibility, fulfillment and the future,

….come Tweet with me

PS- If you think this list of 10 quick questions could help your friend, colleague or sibling with wading through the waves of a change in era, a career choice or the decision to find happiness please forward this e-mail on to him or her. I am a fan of making new friends….and a bigger fan of helping them.

PPS- If this helped you, please pass along to someone you know who would dig on my insights too…..they can join my newsletter of big brainwaves for free at

Plan A – What we want to happen.
Plan B – What happens more often than not.

I often encounter people who are in a state of paralysis.

They can not make a move.

Stuck in the ‘what if’ of decision making.

That place where the clean and solid line between where they are and their Plan A outcome has not yet been drawn.

Or worse, in the place where all of the bridges built from where we stand are to possible Plan B scenarios and we can’t see Plan A for all of the Plan B’s around us.

Worse yet, we are on an island where we have not clearly defined Plan A nor Plan B, but we are so afraid of finding out the Plan B which might accompany a Plan A we really want that we are not even creating Plan A’s anymore.

That was a lot of A’s and B’s…I feel like I am back in calculus class (which I failed twice by the way – but that is a story for another time).

If you are someone who has ever felt like you are having trouble moving forward or making decisions because of any of the scenarios above then you are in luck. Today I will arm you with my secret decision making, fear fighting, opportunity illuminating weapon……

Making a Plan A for your Plan B.

Yes, plan for the worst and decide how you will deal with it.

Make a plan of action for when the ship catches fire in the middle of the sea.

We spend so much time planning for great outcomes (which we know do not always happen) and so very little time planning for the downside of the opportunities which don’t play out as we’d hoped (which we know happens sometimes) and yet, we are surprised that we fear having to deal with a Plan B scenario.

I remember one time when I was looking at a construction job way out in the middle of nowhere in northern British Columbia Canada. I was to set out into the bush on some logging roads and drive about 4 hours to an unmarked location where the government were considering putting in a new culvert (that thing that runs over roads that water goes through). Plan A was to drive out there with no problems. Plan B was to drive out there, get lost, run out of fuel, get a flat tire and have to listen to the same tape over and over again.

What do you think I did?

Got a map, took a Gerry can of fuel, checked my spare tire and jack kit and then tossed a few extra tapes onto the passenger seat. I created a Plan A for all of my Plan B’s.

I was no longer concerned about driving out into nowhere alone. Now all I had were Plan A scenarios.

Think of something in your life you are avoiding or have avoided in the past.

Think of a Plan A that you never move toward for fear of Plan B.

What if you set up a Plan A for Plan B? What if you actually thought through the Plan B scenario to the degree to which it is not longer scary? What if your turn the lights on this monster under the bed?

What if, like me when I started my construction company, you thought, well, if this does not work out I will work at a coffee shop until I can get a job working in marketing in Toronto? Getting that job will take me 4 months and during those 4 months I will take the opportunity to read these 6 marketing books I have been wanting to read. I will stay with my friend X and will go out with her to the following industry events in order to gain greater access to the people I would like to know in the industry. I will work just enough hours at the coffee shop to pay my friend rent and buy food and at least two great outfits to interview in and all of the rest of the time I will be engrossing myself in marketing because that will be my next career.

Does it sound as scary as – “I will fail and have no job and people will judge me for trying to start a construction company and oh my, what will I do if it does not work out?”  This is what most Plan B’s sound like.

So, when people ask me how I do so much or how I have accomplished what I have in the short time I have accomplished it in I often think to myself that I avoid losing time to unknowns by making them known.

Lets say you want something – Plan A. But you seem to not be moving forward, making a decision to pursue it….Look, if you find you have a Plan B scenario and every Plan A you come up with to deal with each Plan B outcome is not going to be ok with you, then you can dump the stalled pursuit of the thing you think you want – that original Plan A. If you can not live with any of the plans you could make to address the Plan B outcomes then you know you will likely never get off of the fence and actually decide to try for that thing you wanted in the first place. Although this might sound a bit heavy handed….truth is, you are wasting your time. Move on with life, find another Plan A.

Tweet it:  “Avoid losing time to unknowns by making them known.” @kelseyramsden

Tweet it: “If you have a dream, turn on the lights and scare the monsters from under the bed, then dream on.”- @kelseyramsden

Tweet it: “Make a Plan A for your Plan B, trust me, the math works.” – @kelseyramsden

Got a Plan A? B? A?

Gonna make one?

In the spirit of getting on with dreams,

PS – I am planning on taking over the world and I need your help. I need you to forward this email to a friend you know in another country/state who might like my illuminations, contemplations and inspirations on having a career/business and life you love. Ask them to sign up for my newsletter and spread the love.

Who doesn’t love a global love-in?

Go on – get in on the love in – pass me on now. Around the world…..

PPS – Have I told you lately that I love you? No, seriously….you are the reason I am able to do what I do and for you I am thankful.

I wasn’t kidding about that love-in.