4 Questions to Ponder Before Making that Big Decision

startup Decision

Can I have them all? Photo: InaFrenzy












My eyes opened at 6.30 am, 30 minutes before my alarm clock was due to chime. Too early for me to get up for breakfast so I lie there. The first thought to pour into my mind was the decision I had to make this week.

It’s official – I was stressed. Know how this feels?

Every so often we’re presented with opportunities and we have to make a big decision which to take. Some of them are no-brainers to accept and some easy to dismiss. But some of them stop and make us think:

What’s the best thing to do?

They can be small, but interesting opportunities – like the chance to be involved in a cool sounding project for X number of hours per week. Or they can be big & risky, like an offer to work on a project that would mean lifestyle or income changes or even a move to another part of the world.

Both of these types of opportunities can lead to difficult decisions – particularly the latter.

And of course, just to make things interesting – the better you get at stuff & the more successful you become, the better the opportunities present themselves (this of course makes sense), and hence the harder the decisions you must make.

I’ve written before about opportunities that present themselves – such as one time I made a bad choice and started a PhD simply because it was a good opportunity rather than what I wanted to do, and how starting this blog leads to a lot of opportunities. To sum both these up – making the right decision is important because it gets you to your goals faster.

Thing is – sometimes deciding what is the right thing to do is hard. It causes you to really dig deep and think is this opportunity is right for you – and forget what other people think.

“I don’t know the key to success, but the key to failure is trying to please everybody.” — Bill Cosby

This can be easy in theory but difficult in practice, so I’ve discovered 4 questions that I ask myself whenever I’m present with a new opportunity. Before I share these 4 questions below, I want to show you the following video about life choices given by Steve Jobs in his 2005 commencement speech – he speaks about how to make big decisions (if you haven’t already seen it – I highly recommend you watch it):

To sum up his main points:

  1. You can’t connect the dots looking forward – only backwards, so you gotta have faith that they’ll connect for you
  2. You gotta love what you do – don’t settle
  3. Ever morning ask yourself: ‘If today were the last day of my life, would I want to spend it doing what I’m about to do’ – if the answer is ‘No’ for too many days, it’s time for a change
  4. Don’t let the noise of other people’s opinions drown your own inner voice
  5. Have the courage to follow your own heart and intuition – they already know what you want to become

How to make the difficult decisions

Whenever I’m presented with an opportunity now – I run it by the following the following 4 questions to see if it’s something I should pursue:

  1. Will it make me so excited that I want to get up at 6am each morning, simply so I can spend the maximum number of hours available in the day on it?
  2. Will it being me closer to my life goals (as opposed to putting them on hold)?
  3. Will I be learning new skills and challenging myself?
  4. Will I be working with great and successful people?

If the answer to all these questions is an instant ‘Yes’ then I’d seriously consider it. If the answer to any of these is No – I’d think twice about going ahead.

And thankfully, once the decision is made you can go back to having a full night’s sleep.

To echo Steve’s send-off: Stay young, stay foolish

Your Turn: Any questions you ask yourself before making a big decision?

About Howard

Howard is a Startup Marketer, Blogger & founder of 3 startups. Currently working with a London based Social Gaming startup.

View all posts by Howard

5 Responses to “4 Questions to Ponder Before Making that Big Decision”

  1. david k waltz Says:


    Often when I am faced with a choice I envision the future under both routes, and ask myself if it didn’t pan out would I have any regrets about not taking the other one. If the answer is no, generally that means it is the right choice.

    As an example, in the 90′s I decided to move to Chicago because I never had lived in a thriving urban environment before. This involved leaving a position on the East Coast of the US. If I opted for the latter, I would have always thought about what might have been.

    By going with the former, I might discover something, I might not, but would always lay to rest the “how does it feel to live in a big city?” question forever.

    I could always leave if it didn’t pan out. I could not always go to the city later if status quo didn’t.

    It is like the country music song – “Have you ever seen a headstone with these words, If only I had spent more time at work”



    • howard Says:

      Hey David – awesome input. Couldn’t agree more, the ‘would I regret if I didn’t…’ is a great way to test if you should do something


  2. Janet Says:

    I know the rational thing makes sense and would be to evaluate and ask yourself logical questions to assess the opportunity/situation…

    I on the other hand am a bit more woo woo than that and try to go on ‘intuition’ and ‘gut’ but always second guess myself (in which case back to the questions would be good)

    So thanks for the questions! This will definitely help my predicament… Actually, I had a feeling your post would help me when I saw the blog title and had to click for more..

    I’m faced with what you call a “small” opportunity but for me it’s big!! nothing like moving to another part of the world, but it’s a chance for me to do something I haven’t really focused on before but know a little about (SEO/social media consulting)… and be a part of a *brand new* marketing agency that is even willing to have me own a % of the company as I grow with them.. Great opportunity for sure, but I have a hard time figuring out what I want to begin with.. Part of me *does* seem to be attracted to an agency mindset and it aligns with some of my daydream/goals but another part wants to go an entirely different direction since my vision is compromised a bit, but I do think they’re open to my suggestions… So, It can’t hurt to try it out!!


    • howard Says:

      Hi Janet
      thanks for all your comments – agree with what you say about relying on intuition, it’s something I’ve actively trying to work on.

      Sounds a really exciting opportunity – entrepreneurs see the opportunity in all situations, I think that makes it even harderfor us to decide on things sometimes (I’m constantly guilty of over-committing myself).

      If the opportunity is a good one and you’ll be learning and working with smart people, then I think you won’t go too far wrong.

      Would love to hear more :)



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