Four Critical Questions To Ask Before Starting a Business

LOMT is an acronym I just made up. It stands for Life On My Terms. Or your terms. Sounds wonderful, right? But just because it sounds wonderful, doesn’t mean it is wonderful. R. Kelly sounds wonderful. I rest my case.

Whether you wish to take on the identity of an entrepreneur, solopreneur, freelancer, world changer, digital nomad, influencer, coach, or even a weasel dick is not my concern. What you are trying to accomplish, dear reader, is LOMT. So let’s talk about these terms.

There are many misconceptions out there that joining the LOMT community is your only path to success, freedom, and wealth—to be considered extraordinary, placed on a throne, and all the rest that gets us aroused.

As a result, we are seeing a stampede of individuals in hot pursuit of LOMT. Unfortunately, due to these misconceptions, we are also seeing more and more failing and falling ill to chronic stress, anxiety, and depression than ever before. And your favourite badass influencer told you it was going to be easy, right!? Wrong.

It’s hard. Real hard. I have seen and witnessed the agony of many who set off in hot pursuit of LOMT. What might surprise you is that I have also seen them overcome with joy when they decide to return to a life of slavery—AKA the Nine to Five—because they have witnessed first-hand the multitude of headaches that come with the territory. As a result, they have a whole new appreciation for the term “gainful employment.”

My goal is never to put you off. It just seems to me that you could save yourself significant stress and potential misery by asking some serious questions before throwing yourself at whatever endeavour you wish to pursue.

With that being said, here are four questions to ask yourself before starting a business which will see you embark on a journey down what is often a very rocky road.

  1. Why?

 Why do you want to do this? There’s the buzzword “Why” which you will use in your marketing collateral to evoke emotion in your customer and quite possibly bullshit them, and there’s your real why which you’ll need to lean hard on when you feel like giving up. You need to get clear on both of them. Bonus points if they actually align.

Most appear to be searching for freedom. Ironically, freedom is the first thing you’ll have to give up. You might get access to greater freedom and opportunity later on in life if all goes well, but the reality is likely a far cry from the pretty little picture you’re painting in your head.

Is it lifestyle, validation, or money? If it’s big money you’re after, you’re going to need an army behind you. If it’s a lifestyle that drives you, looking after an army is probably the last thing you want to do. And if it’s validation you seek, you should seek therapy first.

Who is it you want to help, and why do you want to help them? What is it you want to sell, and why do you want to sell it?

The “how” is the tricky part, but having a good enough “why” will at least give you a shot.

  1. Do you want that much responsibility?

When asked if business was science or art, Richard Branson answered art. Similar to art, you start with a blank canvas. You then have to fill it in and get every detail right for it to work. That’s no easy feat.

You will be responsible for everything. EVERYTHING. Creating is a beautiful thing, but you’ve got to sell what you create. I’ve seen many friends work their asses off and invest a considerable amount of money building what could have been an amazing business only to decide they had fuck all interest in the amount of work required for it to work.

Your endeavour, if it is to have any chance of succeeding, is going to consume bucket loads of energy and a considerable amount—if not all—of your mental reserves, so it helps if you actually want that responsibility in the first place. Otherwise, it will suck.

  1. What do you suck most at?

 Speaking of things sucking, what are the biggest obstacles and challenges you’ll have to overcome?

LOMT requires a hell of a lot of skill. And the rest. There are some lucky bastards out there that do shit, and it just works, but you’re reading what I’m writing, so you’re probably not one of them. However, that’s not to say you can’t be one of them because if you haven’t already noticed,  I’m full of wisdom and very insightful!

You, my dear reader, are most likely your greatest obstacle. That might be a result of limiting beliefs, a lack of confidence, colour-blindness, an inflated ego, perfectionism, fear, or possibly because you’re an asshole?

There’s something you suck at that will likely present huge challenges if you don’t confront it. I’m all for doubling down on your strengths, but if you’re going after LOMT you better be prepared to confront your weaknesses.

Set out to identify what they are and roll out a plan of action to tackle them head-on. If you can’t confront it personally, you’ll need to find someone who can come in and do it for you.

  1. Are you willing to fail?

 If you’re rapping, Eminem’s infamous “success is my only motherfucking option” line right about now then you’re missing the point. To earn the right to write that, he had to fail time and again.

Let us not forget that rejection and failure are two of our biggest fears. You’ll need to face up to them and get somewhat comfortable with all sorts of uncomfortable shit because if you’re not willing to fail, you’ll be willing to do almost anything to ensure your success. I said ALMOST.

Unfortunately, what you find yourself holding back on because you fear failure is likely the very thing that will result in your success. Revisit question three for further clarification.

It’s not about being fearless. Fear is inevitable. But you have to embrace that failure is a possibility and not something you should try to avoid at all costs. You have to take risks. Life’s biggest lessons are gifted to us in our failures. And the biggest wins always carry the biggest stakes.

If you’re not prepared to fail, you’re not prepared to win. In which case, you’ll probably fail by default. Which kind of sucks I know, but the truth often does.

This, I believe, is one of the primary reasons people fail. Failure isn’t the problem. Trying to avoid it at all costs is.

Many successful people get painted as assholes. Many of them are. The others just seem to have the audacity to believe they can do it and go for it full throttle. If you don’t have this personality trait, you might wish to consider calling on an alter-ego that does.

100% commitment will always be easier than 98%. If you’re going to have a crack at this, get ready to go all in. Lean on those that can help you because you will need help. Tell those that put you down and make you doubt yourself to get fucked.

If you’re in the business for likes and validation, then get out before you get hurt.

If you’re looking at someone with a huge following and thinking to yourself, “I can do that” please consider that they too have problems and while you might be able to do what they do, you don’t have their following so you can’t actually do what they do.

There is a lot to consider.  I’m simply suggesting you consider it. The stakes are often very high. Entrepreneurs are four times more likely to have mental health issues, so while the barriers to entry may be non-existent thanks to the Internet, many—unknowingly—are gambling with their health.

The Internet is not Mt Kilimanjaro. It’s Everest. Eleven people died on Everest this year due to overcrowding. The Internet is far more crowded, and it’s killing way more people. Take your work and endeavours seriously, but never forget that life is short. If you find this stuff causing you far more stress than it’s worth, don’t hesitate to get out and do something else with your time here. LOMT is not the be-all and end-all. Live your life, love your life. And whatever you do, do it for you.



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