“A person’s success in life can usually be measured by the number of
uncomfortable conversations he or she is willing to have”
- Tim Ferriss

Sometimes an ugly question can send you down a beautiful path.
These questions aren’t comfortable to think about, because they involve change, uncertainty, and admission that today’s model isn’t tomorrow’s model.
Ugly questions make us assess our situation warts and all, and put our egos aside as we explore the future.
Here are some good questions to grapple with; which ones make you feel uneasy?
Have you got the stomach to explore the question with your circle?

Do we need to pivot or persevere?
Sometimes good advice can be bad for you, if it’s applied at the wrong time.
Perseverance is often good advice – sticking with things when they get tough.
Pivoting is often good advice – changing your mind when things look bleak.
Persevere when you should pivot, and you’ll burn yourself out.
Pivot when you should persevere, and you miss our on a golden opportunity.
The most important word is discernment – which situation am I in?
Seth Godin looks at this in The Dip, a great book on when to quit and when to stick it out.
This simple decision can be the difference between long term success and failure, so it’s worth discussing with your trusted advisors.

Does the business work without donors? Am I the major donor?
I see a lot of entrepreneurs with businesses that made $20,000 of surplus last year, who also aren’t paying themselves.
I ask them if they have any major donors, they usually say “no”.
Then I ask them how much of their time they donated last year, and it usually works out to about $50,000 worth.
So I point out that they are the major donor.
I have no issue with the major donor, it just helps to be honest.
Nobody likes being dependent on a major donor, so it might be worth drafting some plans for becoming independent.
If next year you have an $80,000 surplus with $50,000 of donated time, great.
Margins give you freedom and choices.

Do you want to be a podium builder or monkey trainer?
Let’s say you want to start a new performance; a monkey reciting the works of Shakespeare, perched on top of a marble podium.
Which task do you want to do first – train the monkey or carve the podium?
Will Dayble asked this to one of our accelerator participants, and I now use it with most of our entrepreneurs.
The answer is telling – does this person want to do the obvious thing first, or the hard thing first?
Logic says that the podium carving is straightforward so can be done immediately, whereas training a monkey to recite Shakespeare could take an indefinite amount of time.
But look at it the other way: which one gives you a business?
The monkey without the podium can still draw a crowd.
The podium without the monkey is much harder to monetize.
This is part of the #monkeyfirst movement – doing the hard part first, to quickly determine if the idea has potential.
It’s scarier, but saves you a lot of time and disappointment in the future.
If your proverbial monkey can’t be trained, you want to know that right now.

What can we do now that will make everything easier in the future?
A lot of people have a long to-do list for their job, business and personal lives.
These tasks are probably all valid, but the sequence matters.
There are probably some tasks that are buried towards the bottom of the list (or haven’t even made it onto the list) which aren’t pleasant but make everything easier.
I’m betting these are unpleasant, because if they were then you’d have done them by now.
For example, customer interviews may not be urgent but they can make everything easier.
Same for putting in proper systems, like HR or accounting.
Same for resetting your culture – tough today, but every subsequent day gets easier and more productive.
Same for your online presence – putting in the work to make your brand more visible will have an ongoing, compounding effect.

Should we drop 2 or 3 projects in order to focus on the real winner?
One of the biggest traps I see is people staying engaged with projects because of their potential.
Busy people often have 3-6 of these on the go at once, doing just enough to keep them all chugging along.
The danger here is that they’re all good things – that’s what makes them so compelling.
You know that, if you put your mind to it, you could do great things with this project.
That’s where tradeoffs come in; you can do whichever one you apply yourself to, but not all of them at once.
Which sacrifices are you prepared to make?
Which opportunities are you going to postpone in order to focus on what’s most important to you?
It might involve cancelling plans to open a second location, stepping down from a board, delaying the plans to run a marathon, cutting your low value customers, or pausing your work on the “marble podiums” from the earlier question.
Greg McKeown’s book Essentialism might be valuable for you – teaching you how to cut back on most things in order to really focus on the activities that fuel your success.

Do we need to learn a skill or hire a professional?
A great example of discernment – sometimes you need to learn a skill, sometimes you need a professional, and the wrong choice is really expensive.
It’s expensive to hire a professional when you should learn a skill, e.g. content creation.
You can pay someone to write an article for your company’s site, but one article won’t do much compared to an ongoing pipeline of genuine content.
It’s expensive to learn a skill when you should hire a professional, e.g. creating brands and visual identities.
You don’t need to become an amateur designer, you need to pay for someone to create something excellent.
How important is it that the skillset sits within your team?
Is this something that will continue to pay dividends, or will it be an expensive hobby disguised as a business decision? 

What should we test next?
Coming up with new ideas is fun, whereas testing new ideas feels like a reality check.
I bet you and your team are full of ideas, so which test are you going to run next?
What’s a test that proves the idea to be true?
What should you measure?
What’s the pass/fail criteria?
You might find the Test Card useful for designing something cheap and quick. 

What’s the next pilot we can run?
A lot of people want to set aside time for planning – like a team retreat, offsite day or strategy session.
Fewer people want to put aside time to run a pilot, despite it being more useful than more time fine-tuning the irrelevant details.
Instead of thinking about the plan, is it better to run a pilot and cut to the chase?
What if it shows you what customers love?
What if you’re pleasantly surprised by the results?
What if it kills some of your cynicism?
What if it saves you three months?

Gun to my head, can I compress the next 10 years into 6 months?
Now you see why these are ugly questions.
This question from Peter Thiel conjures up strong imagery, which highlights the false assumptions we tend to make about time.
Why do you forecast slow and steady progress?
Why do you keep assuming things can’t happen until you’re “ready”?
What if there was a way to massively compress the future into the remainder of this year?
If this were possible, what would you give for such a huge advantage.
Changing your expectations around time can lead to a massive improvement in your work, and it costs you nothing to change your mind.
Some potentially helpful prompts include:
·      What tasks aren’t really necessary?
·      What are you planning to do based on the expectations of others?
·      What can you do in a quick-and-dirty way instead of the long-and-thorough way?
·      Where can a modest amount of money save you several months of time?
·      Where are you relying on the timeline of a partner (e.g. supplier or co-deliverer)?
·      Are you waiting until “everything is ready” instead of launching a “minimum viable product”? 

What project are we building that we may never see completed?
I heard Graham Ross use this question, he called it “Cathedral Thinking”.
The world’s great cathedrals generally took over 100 years to build, which isn’t particularly interesting until you think about the mindset of the founding team.
They started something that even their grandchildren may not see completed, and yet they put their lives into the project.
It’s tempting to use five year horizons to measure your progress and your impact, but maybe that’s an irrelevant scale.
What are you working on that might take 100 years to complete?
What can you get started that other people will get to finish?
How does this change your objectives, measurement and choice of project? 

What would I do/have/be if I had $10 million?
If you were able to take money out of the equation, how would you spend your days?
Which sort of work would you find interesting and fulfilling?
What labels would you want attached to your name?
What would a typical week look like?
What would you want to achieve?
Is money the real barrier stopping you today?
How much money do you actually need?
Does a mortgage and a nice car mean more to you that this alternate path?

Do I actually want two small cakes?
People often talk about the challenge of “Having your cake and eating it too”.
Maybe what you want is two small cakes?
One to eat, one to keep.
This question can revolutionise how you approach problems.
Maybe there isn’t one perfect solution to your situation, maybe it needs two specialised solutions.
Maybe you’re actually building two small businesses, or serving two different markets, planning two different holidays, buying two different pairs of shoes.
Giving yourself the option of dividing and conquering can feel weird at first, but it might unlock two great ideas instead of one giant compromise.

Am I afraid of selling? Why?
Sales is seen as a dirty word, but not for good reason.
Do you dislike selling, or do you dislike selling something you don’t believe in?
We sell things all the time, suggesting the restaurant for a group dinner, recommending a new TV show, encouraging people to travel to a great destination, or giving advice to a friend about their career options.
We sell things all the time, we accept money all the time.
You’re probably feeling icky about selling someone the wrong thing.
Good!
This should feel icky!
The icky feeling is the response of a good person, it’s your empathy and decency outweighing greed – that’s why you see so many sociopaths in multi-level marketing.
Perhaps the difference is “who’s doing who the favour”.
When we feel like the customer is doing us a favour, sales is creepy.
When we feel like we’re doing the customer a favour, sales is gratifying.
Maybe you don’t need sales training, maybe you need to improve your products and services so that they’re genuinely worth recommending.

Am I building a business or a job?
If you start a company that doesn’t work without you being there, you’ve built a job.
This isn’t necessarily bad, it just makes you self-employed rather than an entrepreneur.
This is my situation – my freelance work isn’t attempting to be a company with employees, it’s designed to let me do cool things with cool people, and I’m honest about it.
For some people this approach is wildly inappropriate, especially if your aim needs a scalable business or a large team.
If you want a business rather than a job, then you might need to redesign your operations so that they’re not reliant on you.
This has the added bonus of allowing you to go on holiday – I’ve never heard anyone object to that.

Am I actually creating assets?
Following on from the last question, a business needs assets to run, and in order to one day be sold (don’t freak out, you have lots of options).
The role of the entrepreneur is to create assets that support the business, something that is often in the category of “important but not urgent”.
These assets might be tangible, such as your equipment or your inventory, or intangible like your brand and reputation.
The book 24 Assets by Daniel Priestly gives a great overview of the topic, and all of the various categories of assets that you need to start creating (e.g. funding, marketing, culture, systems, products and IP).
Is this something you’ve been neglecting?

Do I actually have the right support around me? Is there a gap I need to fill?
Your circle is not fixed – it will change over time whether you like it or not.
You can play defence at let it happen passively, or you can be proactive and recruit good people around you.
This includes your colleagues, employees, friends, partner, family (yes this is a choice), mentors, content creators, psychologists, and clubs.
Is there a deficit today?
Are you missing support in some areas?
Do you have negative influences that need to be reduced or cut?
You know the answer already, the ugly question is are you going to take action?

Is that a dream or a goal?
They say “A goal is a dream with a deadline”.
Which do you have?
What might be some milestones and deadlines that turn your intangible dreams into clearly defined goals?
My suggestion is to choose goals that are within your control, e.g. actions you can take, rather than relying on you “getting picked” by someone else.

Am I hunting antelope or field mice?
Tim Ferriss uses a great analogy from Newt Gingrich, I love his wording so I’ll keep it here:
A lion is fully capable of capturing, killing, and eating a field mouse.
But it turns out that the energy required to do so exceeds the caloric content of the mouse itself.
So a lion that spent its day hunting and eating field mice would slowly starve to death. A lion can’t live on field mice.
A lion needs antelope.
Antelope are big animals.
They take more speed and strength to capture and kill, and once killed, they provide a feast for the lion and her pride.
A lion can live a long and happy life on a diet of antelope.
The distinction is important.
Are you spending all your time and exhausting all your energy catching field mice?
In the short term it might give you a nice, rewarding feeling.
But in the long run you’re going to die.
So ask yourself at the end of the day, “Did I spend today chasing mice or hunting antelope?”

Which one have you been chasing?
Which one should you chase tomorrow?
Can you find someone to teach you how to hunt antelope in your industry?

Can we start a different business that we can push downhill?
Now we’re getting really ugly and really valuable.
Seth Godin talks about businesses that you have to push uphill – when you need to expend lots of energy to make every sale.
No natural customer acquisition.
No natural market.
No natural retention.
Arguments over price.
Pushing uphill is exhausting – is there a business that you could push downhill instead?
Something that people want to buy?
Something that has customers lining up before it opens?
Something where people share the story without being coerced?
Is this a version of your current business?
Or is it worth starting something new that you can push downhill?

What bullshit excuses do you have for not going after whatever it is that you want?
Steven Pressfield created a name for the voice in our heads that doesn’t want us to change – he calls it “The Resistance”.
The Resistance is creative, throwing up a range of good reasons why you shouldn’t make things, change things, improve things, or take any form of risk.
Once you name it, The Resistance loses some of its power, but you still need to actively overcome this inertia through determination.
Tim Ferriss asked the above question to his audience – what excuses are you making for yourself that are holding you back?
Are there genuinely people trying to block you, or is it a product of your own mind?

I hope a few of these questions sting a bit, that’s where progress comes from.
My encouragement is to channel that discomfort into action.
I’d start by talking the questions through with a mentor or trusted advisor, to get their perspectives and refine your initial ideas.
Ugly questions can lead to beautiful outcomes, if you’re brave enough to be uncomfortable today.