Should I Start a Startup

Should I Start a Startup?

Are you asking ‘should I start a startup’? Or even, if you fell into your startup by accident, ‘should I continue’?

Well, should you carry on? And what is the best career advice for startup founders?

Maybe it will happen during summertime?

You are away from work, walking to the beach, hearing the waves on the sand or the wind in the dunes and suddenly it dawns on you…

What am I doing?

Or maybe, it will happen when you are halfway down a snowy mountain on a winter break and you ask…

Should I carry on?

Both are great questions. And both questions need to be answered.

So, here’s a little thought experiment I designed to help founders and would be startup entrepreneurs answer those questions.

So, take a moment whilst lying somewhere hot or sitting in a snow cold bar and play this little game:

The Values Game

Sort, in order of your highest to lowest priorities — these five values:

i.) Money
(ie having lots of money – if it’s your top priority, the amount really matters. If it’s your bottom priority, the amount doesn’t matter at all!)

ii.) Reputation
(ie. what people say about you, the applause at the end of a speech, your social media ‘likes’. Do you care? A little? A lot? Like, really a lot?)

iii.) Power
(ie. how many people’s lives do you directly affect? Say as a CEO, Head Teacher, Politician, Inspector? And is this important?)

iv.) Status
(ie. the suit you wear? The bag you carry? The car you drive? The Apple brands you own? Or perhaps the awards and medals you accumulate? Do you care? If you already know your next car / phone / headphones brand – this will be important to you.)

v.) Meaning
(ie. the difference you are making in the world? Or, to the people around you to the environment? Even if they don’t know or don’t appreciate it?)

Now re-sort:

Once you think you have your Value’s in order from (top) most important to least important (bottom) ask this:

Would I be willing to give up x for y‘. So, if you place Status first and Money second, would you be willing to give up Status for Money?

  1. Status (I will give up Money for Status)
  2. Money

Likewise, if you place Money above Status, would you give up Status for Money?

  1. Money (I will give up Status for Money)
  2. Status


Then ask a trusted friend or associate to choose your list of priorities for you.

Compare and contrast the priorities they see you holding with the priorities you see yourself holding.

If your trusted friend orders the values differently from you, then it is possible that the question of should I start a startup or change my career is coming from a mis-understanding of your own motivations?

Look at the value that you put at the top — is it Money, Power, Meaning, Status, Reputation?

Does your career path or startup company place that value above all others?

Then look at which value you put bottom — is it Money, Power, Meaning, Status, Reputation?

Does your career path or startup company place that value below all others?

Do your values and your career and / or startup match? If not, that’s the problem…

Other people’s values

Discovering your values – and then discovering your colleagues or co-founder’s values helps you understand a lot of other issues too.

For instance, it is highly likely that you miscommunicate with people who treat your lowest priority as their highest priority.

If you work with other people, you may be missing what really motivates them — because, we all, naturally, think everyone should be like ourselves, when they clearly are not.

Equally, if you are in the middle of co-founder fights – then you will be asking the question ‘should I / we continue’ – when in fact, the better question is – how do each of us priorities these values – where do we differ and what challenges and issues does that leave us with?

I wrote a piece on how to overcome co-founder fights here.

How does this help answer ‘Should I Start a Startup’?

In truth, this Values game helps each of us understand if we are starting the ‘right’ startup. In other words, is our startup inline with our values?

So, the better question to ask is: ‘Is this the right startup for me?’

This question also applies to the kind of customers that your startup seeks to attract.

Hence, if you are a startup founder starting a startup and building value products and services that people want to buy — have you understood the real motivation of your clients?

For instance, how would you list the priorities for your perfect client or customer?

Let me give you an example — my lowest priority is Status — I have never been able to get my head round the fact that some people covet cars that cost $zillions or handbags priced in $millions when there are fabulously engineered and designed cars and handbags for a fraction of the price.

However, my struggle to understand the motivation here is because Status is my lowest priority but for many others it is top or near the top.

This means I need to avoid startups which are selling some kind of Status symbol. It just isn’t my thing.

I also need to pay particular attention to Status as a motivator for founders and clients I work with — because, otherwise, I am likely to miss opportunities to have an impact.

Equally, take Power, the desire for Power explains why extremely wealthy (Money) business people leave exceptionally well paid roles for (relatively) poorly paid public service. Although, in some cases, the switch can be driven by a desire or quest for greater Meaning.

Another way of putting this is to say that if you don’t put Money as your top value – then is Crypto right for you (okay, there will be exceptions, but most crypto businesses are about getting rich). Likewise, if your startup is a deep tech startup, then is Meaning or Reputation high in your values list?

If I put Meaning top and Money bottom – should I start a startup?

You might expect me to say no, in the case that you put money bottom and meaning top? But you’d be wrong.

Yes, a few years ago, Money and Status – often proving other people wrong (especially, absent fathers in the case of many serial founders) were key.

But today, the startup opportunities for environmental, social or political impact are big. And there is money available too.

So, play with your list of priorities — ask others — ask your colleagues and ask you customers and clients.

Look for the surprises and insights.

Here’s the answer…

So, the answer to our question – should you start a startup – is both yes and no! If your startup is aligned with your priorities or values – then, it will be rewarding, fun and possibly successful. And, if you work in a space that deeply interests you and connects with your values, then, if this startup doesn’t succeed, the experience you gain will almost certainly open new doors and new opportunities for you.

The key here is not to give up your job / career and startup because a) it looks like a cool thing to do or b) because everyone is doing it or, most importantly, c) because you don’t like your job – if – you don’t know why you don’t like your job.

It is inevitable that many startups were begun because of nothing better to do or dissatisfaction with what you have. Unfortunately, that isn’t a reason powerful enough to get you through the many down moments in startup life. You need something firmer.

Other people have tried to answer the should I start a startup question too – where they take a more ‘will it work, will it add to my career’ approach. And it is a good approach. However, it doesn’t beat working out if your values are aligned. Because, the key to startup success is the ability to pivot, to focus, to move on, to keep it lean and to be hungry. Those qualities are easier to access when you are aligned with your values and priorities – they are impossible to access if your values and priorities conflict with your startup’s purpose.

Then check in, where am I going with my career or startup?

Should I start a startup?