This is undoubtedly the most difficult, and yet most rewarding, blog post I’ve ever written. I’ve found it an incredibly useful exercise to help me re-focus on my own goals for the future – and how I plan to achieve them – at a time when I was feeling particularly unsure about whether I was prioritising my time, energy and money on the right things. It’s certainly not easy answering these questions with honesty, genuine honesty, and they do require you to face up to some uncomfortable truths, but having answered them I feel reinvigorated and eager to start on turning my ambitions into reality.

Before I get into my answers, I’d like to thank Al Humphreys for creating this list of questions and for continually inspiring me to challenge myself and live on the edge of, and beyond, my comfort zone.

Here we go then… 20 questions worth answering (I hope you consider answering them too)…

1. Do you earn enough money?

No. On a basic level, I’m not earning enough to be secure financially. On a more aspirant level, I’m not earning nearly enough to reach my ambitious goal of financial independence by the time I’m 40, or to enable me to invest into bringing about positive social change as I desire. However one of my businesses is developing well and the other is due to launch soon – so the foundations are certainly laid for this situation to change dramatically.

2. Do you enjoy your job?

It’s a delight to be able to offer a resounding ‘yes’ to this question. Starting my own business is possibly the best decision I’ve ever made. The lifestyle and freedom it brings is certainly compensation for the (currently) much lower income. Obviously entrepreneurship has its low moments – but these just serve to make the highs even more enjoyable.

3. Do you prefer Saturday or Monday?

In all honestly there is now very little difference (outside of cricket season at least!). If I have a free weekend I’ll quite happily spend it in ‘work’ mode. Equally being self-employed affords me the opportunity to use my weekdays flexibly and regularly take time off. That said, I have become quite fond of first thing on Monday morning – the chance to plan for the week ahead and get stuck into a new week of opportunity…

4. What would you like to be doing one year from now?

I’d like my first business, Big Green Fox, to be trading at a level which means I can draw a more reasonable salary. I’d like for my second business, Goalvanise, to be well on its way to becoming commercially viable. I’d also like to be continuing to challenge myself with ‘microadventures’ but also be starting to undertake more challenging adventures. I also still want to be achieving life goals across all areas of my life.

5. What would you like to be doing five years from now?

Still very similar in terms of lifestyle, although starting a family could be one possible major development! I’m aiming for both businesses to be thriving and earning me an income sufficient to start investing in other social enterprise projects. I’d like to have gained the skills and experience to be able to undertake much more ambitious adventures – and of course still be pro-actively ticking off my life goals.

6. What would you do with your life if you were a billionaire?

I’d convert both my businesses to a not-for-profit model and employ specialists who could better realise their social aims. I’d play a more distant role in their management to free me up to spend more quality time with friends and family, undertake full scale expeditions, take long trips in distant lands. I’d also become an angel investor and help grow other social enterprise projects – and help my friends and family realise their own ambitions. I don’t crave any of the excesses associated with wealth, so I can’t imagine my lifestyle would change too much otherwise. Is it possible to live a modified version of this life anyway? To a very limited extent, I already am.

7. How much could you cut your outgoings by?

My everyday outgoings have already been considerably streamlined. I could possibly spend less on food but don’t really spend much on anything that isn’t closely associated with my businesses or life goals and adventure/travel (much of this is done extremely frugally too i.e. hitchhiking, camping etc).

8. Do you have enough spare time to do the things you really enjoy?

Only for short periods of time – I struggle to plan in anything that would take longer than a week because of my commitments to my business(es). It’ll be difficult to change this until I’m in a position to employ staff and delegate work.

9. What takes up a lot of your time but is neither unavoidable, rewarding nor enjoyable?

General admin for Big Green Fox. Unfortunately we’re not in a position to pay anyone else to do this yet.

10. What mildly pleasant, but pretty pointless things do you fritter too much time doing?

Anyone who knows me well will know I’m guilty of debating politics on Facebook far too much. Although this is enjoyable, I’m sure this energy would be better spent elsewhere and is something I need to make an effort to cut out. Equally I spend a lot of time reading about politics and current affairs online. Again, this is rewarding but is time that could be spent better. It could be argued my personal blog is pretty pointless as I don’t draw an income from it – but I enjoy writing it, it holds me to account in leading a full and varied life and, as I’ve been told, it is serving to inspire others.

11. What would you like to do more of?

More proper mountaineering, long expeditions, and spending time in countries outside of Europe (even while managing my businesses via ‘the cloud’). Also, making videos! Not with money in mind, it’s just fun! Plus helping other people to start business projects, seek adventure and achieve their life goals (the launch of Goalvanise should certainly help with the last two).

12. What motivates you to do something well?

Personal pride and satisfaction. Public accountability (hence my Life List online). I particularly thrive when a challenge is competitive.

13. Who do you envy, and why?

People who started doing amazing things early in life e.g. setting up a business while at school. People who have been able to make a living out of traveling the world and seeking adventure. People who earn a living whilst living on a beach in Bali! People who are better than me at things I want to be good at (not a good trait, but it does also spur me on to become better). Oh and my friend Chris who’s currently cycling around the world.

14. If you were 100 and looking back on your life, would you be happy with a life well-lived?

For the most part. I think I’ve achieved a great deal with my life so far, and done and experienced a great many things. I don’t have any major regrets although am always painfully aware that I could be leading an even fuller life, be more efficient with my time etc. I try to live by this quote:

“In twenty years from now you will regret the things you didn’t do far more than the things you did. So throw off the bowlines, sail away from the safe harbour, catch the trade winds in your sails. Explore, dream, discover.” Mark Twain

15. What makes you proud, satisfied, and content?

Proud: the ‘highs’, those magic ‘ this is working’ moments, on the entrepreneurial rollercoaster or when I hear that my actions have inspired someone to do something new / challenge themselves.

Satisfied: challenging myself, both physically and intellectually, and then succeeding or planning for my next project / adventure.

Content: simple pleasures – a couple of cheeky ales, a good meal or a shared experience with those closest to me.

16. What makes you frustrated, bored, and unfulfilled?

When my life feels stagnant and I’m not making the most of my time and energy.

17. What would you do if you had more talent?

Write more. Speak more. Inspire more.

18. What would you do if you had more guts?

Write more. Speak more. Inspire more.

19. What would you do with your life if nobody was watching, judging or commenting?

This one really has me stumped! I’m torn between a) Little different from what I’m doing at present and b) Get on a bike and cycle…

20. What are you going to do about all this?

Rise earlier, procrastinate less, prioritise better

Run more, cycle more, swim more

Continue to grow Big Green Fox into an established business

Launch Goalvanise and work hard to make it commercially viable

Use Goalvanise as a mechanism to write and inspire more

Continue to microadventure… but make them progressively more inventive and challenging

Organise an annual expedition with friends

Review my Life List annually and try to achieve 50 Goals every year

Explore more, dream more, discover more…


If you’d like to answers these questions yourself, click here for Al’s original post which also contains the prompts to help you answer.

About Jon Maiden

Founder of Goalvanise which enables people to create their Life List online, and inspires and supports them to achieve their life goals. Check out the Goalvanise blog here or my personal blog here.

8 responses »

  1. Interesting reading! Everything is relative but being able to commit to something extracurricular for a whole week is something I can’t begin to imagine.

    Good luck with financial independence by 40. I’ll be happy if I ever get there!

    • Jon Maiden says:

      Hi Greg, cheers for reading. Financial independence doesn’t necessarily involve a lot of money. It’s more about earning an income that doesn’t require me to be sitting at a desk X hours per week. So I could be earning little more than £30,000 a year and still be financially independent. I desire breaking outside of the time for money paradigm – not the money itself per se. Then I’d be able to take off much longer than a week whenever I wanted. That’s the dream.

  2. Gav says:

    Great post (as usual) Jon!

    I enjoyed reading each and every post, many of which I can strongly relate to due to me having similar ambitions to grow my first, and launch my second project/company/future.

    On point 11, I am one of those people who is inspired by your blogs, so for that reason, and the reason that by writing it down and then telling people you are going to do something, makes you much more likely to achieve it, as the knowledge that people know you have failed is something which adds more motivation to succeed.

    When is Goalvanise launching?

    Keep up the good work!

    • Jon Maiden says:

      Hi Gav,

      Thanks as always for your feedback. It’s always great to hear that valued friends enjoy reading my blog – and wonderful to hear that you find it inspiring. It certainly provides a motivation to keep it going.

      We’re hoping to have the Goalvanise blog running within the next week or so with a view to getting a bit of interest before the main site is launched. This side of Christmas is what we’re hoping – but who knows! It’s already well over a year overdue…

      Speak soon,


      PS Any chance you can make the weekend in the Lakes (first weekend of Nov)?

  3. wanderoneday says:

    I really like the list of questions (and your responses)! I think it’s awesome that you’ve started your own businesses. I’m always daydreaming about breaking out of the 9-5 at a desk cycle, but I keep holding myself back. For one thing, I really like the work that I do – I just don’t like doing it on such an inflexible schedule. But the problem with a job like engineering is that you need to be available when your clients are available – since most of our clients are municipalities that work 9-4 M-F, I’m pretty much stuck during those times. But I have to admit I love the steady work because it allows me to plan my vacation time in advance, and then daydream about travel for months!!

    • Jon Maiden says:

      Yes, there’s definitely pros and cons of both lifestyles. The flexibility is certainly a worthwhile trade off for the (presently) lower income. I’m not sure how long I’d be able to sustain it – but hopefully my plans to grow the businesses will pay off. I do always remember how good it felt being on holiday and knowing I was getting paid for it! But equally, it’s now nice to hear of income coming in whilst I’m traveling (and knowing I’ve earned that myself). Time will tell whether it’s all worthwhile though…

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