• How do you go about getting your first speaking gig? And how do you plan your talk? – Connor
• If I remember right, then you were saying that you did hundreds of free speeches at schools during your cycling around the world journey. I’d like to know what exactly you talked about? Did you do chronological presentations about that journey or did you have certain topics/messages which you wanted to deliver to the kids? And how long did you usually speak? – Chris
• How did you first go about arranging all the talks you first did after your trip?
• I’ve got an awesome collection of stories and anecdotes and I’d love to share these. But I am not a confident public speaker and have actively avoided it for a long time. Is it irrational to be terrified of speaking to a bunch of school kids? For how long did you tour around schools before beginning to charge for your talks? – Pete

But that’s not how I went about it!

My first talk took place a few days before I had anything interesting to talk about. It took place before I had done anything at all!

My Mum assembled her local WI in our living room to hear all about the marvellous bicycle ride around the world that her son had not yet even begun. I was deeply embarrassed and at a loss to think what on earth I could talk about. But I figured that going ahead with the talk would pretty much pay back 24 years of free rent, food, and the joys of childbirth, so I scampered up to my bedroom to take the world map off my wall. I used pins and string to approximate my imagined route around the world, manoeuvred my shiny new bike and panniers in front of the mantlepiece, and began winging it.

LESSON: it helps if you have something interesting to talk about before you decide to become a speaker. But, failing that, there’s nothing you can do about being a beginner except to begin, and make the best of things. 

I had no intention of becoming a ‘speaker’ when I set off on my bike. But I did want to raise funds and awareness for charity and therefore needed to tell my story somehow.

When I reached Istanbul, a school invited me to give a talk to the kids in return for a donation to the charity. The idea had never occurred to me. But I said, ‘yes’, and the next ten years of my life began.

How did I get that first talk? The friend of one of my mum’s friends’ daughters lived in Istanbul, let me stay at their home, and had a kid at the school. LESSON: accept whatever opportunities come your way, look for opportunities, personal links (however tenuous) are critical for getting your toe in the door.)

What did I talk about? As with the talk for my mum’s friends in the living room, I didn’t yet have a lot to tell. But at least now I had two months’ of tales from riding across Europe. I made my first ever PowerPoint slideshow, put my tent up for the kids, showed them my tiny camping stove and inflatable mattress, and answered what would become very familiar questions about wild animals, favourite countries, and poo. LESSON: do your first talks for free in order to learn what the audience found interesting, improve, repeat. 

I ended up spending several days speaking to all sorts of groups of kids in that school. The talk lengths varied (as they always do) from too short to too long. I once cycled a considerable distance out of my way to speak at a school in Kenya and was given five minutes. More than once a frazzled teacher saw me as light relief and sent me out in front of the lions for 90 minutes or more (whilst they did their marking, no doubt.)

Over time I have settled on preferences of 30 minutes max for young kids, 45 minutes for teenagers, and one hour for adults (each with 25% of the time for questions.)

Before pedalling away from Istanbul I asked the school for a reference. I asked if they could personally connect me with any other international schools on my route. And I spent many a late night emailing loads of other schools which lay on the next leg of my ride.

And that’s it. I simply repeated and polished this whole process for the next 44,000 miles. LESSON: make an effort to secure references and recommendations for future talks. Work really hard to get yourself noticed by other schools / organisations / businesses that might be interested in what you have to say. 

This pursuit of references and word of mouth recommendations is critical and continues to this day, almost two decades since my first talk. Whether it’s collecting speaker feedback, asking people to review my books and podcasts or forward my newsletter to a friend (please do!), every aspect of becoming a viable working adventurer depends upon me asking people to take action on my behalf and (hopefully) offering sufficient in return for this to not feel irritating or parasitical. (If it does, you won’t last long.)

Bring props if you can.

Show photos, but not too many. (Regard them as prompts and titivation, not a crutch.)

Use the other 25% for audience Q&A so that the audience can hear about what they care about, not what you guess they might care about. (If you are nervous about a deafening silence of zero questions, you can prime a friendly audience member or two with questions to kick things off. I have never done a talk where there were no questions at all, but I have sometimes had to cajole the first question out of someone to break the ice.)

Over time the delivery of your anecdotes will improve. Pay very close attention to the body language of the audience to decide which stories deserve expanding and which should be culled. Treat the Q&A sessions like an invaluable Customer Survey and pay attention to what they are most interested in. Incorporate those aspects into your main talk next time. Cull even your most heroic, mock-humble, audacious yarns if nobody cares but you!

I continued in this vein for four years, giving over 300 unpaid talks on five continents around the world to raise funds for the charity and, often, in exchange for my bed and breakfast. As the trip progressed my anecdotes improved, and so too did the tone and focus of my delivery.

I learned to tailor my talks according to different age groups, to the venue, to the expectations of the audience (are they here to sit back and be entertained, or are they here to be challenged and to learn?), and the expectations of the organiser.

I can certainly recommend you trying to give a Pecha Kucha talk. Compressing your story into 400 seconds teaches you a lot about what is important to include in a one hour talk.

I hope that you can see some patterns and glean some insight: that it’s not a mystery it’s not all nepotism, but that it takes a long time and that your contacts are certainly helpful. You need to be clear about how you will earn enough money before you are earning enough money from your speaking. 

1. Free talks in my village hall, nearby towns (on the back of a few local newspaper and radio interviews), and schools.
2. Free talks at schools via teachers I knew, in exchange for references / recommendations. It’s a good period also to offer yourself to Skype in the Classroom and speak to kids worldwide. (I’ve written some tips about speaking in schools here.)
3. As above but daring myself to be so arrogant as to request £50 for my talk too.
4. Email mailshots to schools, gradually increasing my fee until I began meeting resistance to it: about £200, I recall.
5. Talks at travel clubs, cycling clubs, universities etc. I also phoned up the big travel exhibitions and asked whether they had any unsold, unwanted, tiny, out of the way exhibition stands that they might be kind enough to allow me to fill with my photographs, bicycle, and charming sales patter to thousands and thousands of passers-by about my talks. (See the flyer I was handing out, below. I couldn’t afford a designer or proper printing!) My girlfriend sneakily printed out some of my photos in A3 on her office printer, I bought some blutack and pedalled off to peddle myself. Those events were ridiculously exhausting and soul destroying! 😂
6. My diary began to fill up with school talks, charging £400 for a talk or £500 for a day of talks.
   I learned that it’s best to try to speak only to a single year group rather than the entire school. If you talk to everyone you won’t be invited back for 5 years, but do a good chat to the Lower Sixth and you’ll become a fixture in the annual calendar for years to come.
   There are, effectively, an infinite number of ‘Lower Sixths’ (or whatever age group appeals to you): I had reached a point whereby I now had a sustainable income for as long as I was willing to tell the same tale. My record was visiting seven different schools in one day: exhausting, ridiculous, fun.
   Speaking in schools is a brilliant, brutal education for a speaker. If you’re bad or boring then the kids will be sure to let you know!
   On the other hand, if you can hold a classroom pin-drop silent then 1000 executives in a theatre is a piece of cake. (You’d be surprised, also, how little you need to change the messaging or tone between the two groups!)
7. I decided to progress onto corporate talks for the simple, greedy fact that I could get paid a lot more. I began hustling speaking agencies, trying to get put on their books.
   This is a very crowded and competitive world.
   Most agencies already have plenty of adventurers on their books. Through perseverance I succeeded in getting a few bureaus to take me on. All I had to do then was sit back and wait for the Ferraris to pile up in my driveway!
   …Sadly not: merely being on a bureau’s books does not guarantee talks. Some haven’t got me a single booking in a decade! But you don’t have to pay them so it is worth a pop.
   What tends to happen is that somehow (luck, illness of another speaker, persistent pestering) an agency puts you out for a talk. If you do it really well (better even if you can persuade someone from the agency to come and watch you) then you become flavour of the month for a while and start getting loads of bookings from that agency. Until some new, young punk hustles their way in front of you in the pecking order and the phone calls dry up once again.
8. Sometime around now I began working with a speaking agent to organise my talks. I’ve worked with Caroline now for about 12 years and it has been an excellent relationship.
   Caroline gets a fixed 20% slice of whatever pie she can negotiate for the talk and sorts out the stuff I’m terrible at (arguing about money, signing contracts etc.) Whether or not you prefer to have a speaking agent will depend on how comfortable you are with those things. Personally I’ll hand over almost all of any pie to get out of paperwork, awkward conversations or conference calls!
9. Getting my foot in the door with the world of corporate speaking mostly came from other avenues than the speaking bureaus.
   Cold calling never worked, nor did massive email mailshots.
   Word of mouth from my talks at travel shows helped. Parents who heard me speak at school events might book me to visit their company. In the main, however, enquiries come via my website.
   I smartened up my website to look more professional and seasoned than I felt.
   And I began a concerted mission to get myself placed high on the Google search page when people typed in phrases like, “Motivational speaker adventurer” [Number 2 on Google}, or “heroic, handsome speaker” [less successful].
   I knew that my website was the only thing I had total control over, the little bit of internet real estate where I was not in the hands of some other gatekeeper.
   I began spending 50% of my time blogging, to build up content, to establish a reputation in my niche, to grow an audience (you can’t read 1000 True Fans too many times), and to make myself noticeable to people rummaging around online for somebody suitable for their speaking event. I included the word ‘motivational’ and ‘speaking’ in much of what I wrote (such as this).
10. Repeat this for many years (and remembering always to garner references and recommendations of other people to contact) and I became pretty busy with well-paid corporate events. I finally felt able to relax and be confident that enough talks would come my way this year and next year too.

One way of earning income from speaking that I have occasionally toyed with but never committed to is going on a tour. I like the idea – a few concentrated weeks on the road, pootling round bookshops in new towns by day, giving a talk at night, selling a heap of books at the end, a larger slice of the pie than usual. But (as always) I’ve shied away from the mounds of admin, planning and financial commitment. Other adventurers have done it very successfully though: Andy Kirkpatrick, Lev Wood, Ben Fogle, Steve Backshall, and Mark Beaumont leap to mind. It’s certainly something I would like to do one day (if someone else will do all the hard work for me!)

During my 15 years of earning an income from speaking I am often asked to speak for free. This is a conundrum faced by speakers, artists, designers, and photography, yet not for some reason for everyone else with a job: dentists, lorry drivers, teachers etc. Here’s how I approach this issue:

• By all means do as many free talks as possible in the service of things you care about: charities, Scout groups, whatever. For years I had a Pro Bono page on my website explaining that I did 10% of my talks for free (which also helped me say ‘no’ with a clearer conscience to numerous requests).
• By all means decline invitations when they plead poverty yet come from ludicrously wealthy schools or businesses.
• Feel free to decline invitations when the offer in return is ‘good exposure’. This is really common. And yet do also consider speaking for free at events where there will be sufficiently good exposure to make it worth your while, if you need exposure at the time. I am usually more happy to do unpaid work when it will live for a long time on the web and reach a wide audience (like this).
• When you are speaking for free, look around the venue and ask yourself, “is anyone else here doing their best work for zero pay?” Are you benefiting sufficiently from the learning experience, the contacts, the audience? If not, you’re a chump!
• If in doubt, consult Should I Work for Free?

If you’d prefer a blog, dip into  Nancy Duarte, Presentation Zen, and 30 20 10. Above all, I’d recommend you watch other people speaking and work out for yourself what they do well, what feels phoney and over-rehearsed, and what they can teach you. Search the TED archive by topic, by recommendation, or sheer weight of numbers. If overly-polished, overly-earnest Californians begin to grate, head to a Welsh cowshed to figure out how to go from where you are to where you could be.

OK, so now you are ready to start planning your own talk. It’s not an easy process. I spent two whole weeks putting together these 20 minutes.

Mark Twain allegedly wrote to Winston Churchill (or something like that), “I didn’t have time to write a short letter, so I wrote a long one instead.” 

The same holds true for giving speeches.

I could very easily stand up and blag an hour’s talk with zero preparation (not that I would ever do that, I hasten to add!), but crafting an effective 10-minute talk is a fiendish exercise in focus and paring away.

The best way to prepare for a long talk is by preparing for a short talk. If you can distil your key thoughts and main messages into a Pecha Kucha format (20 slides scrolling every 20 seconds) then you are well-placed to do an hour-long Keynote.

Remember that far fewer people say, “I wish that guy’s talk had been longer” than “I wish that guy’s talk had been shorter.”

Begin by asking yourself some questions:

• What are the key messages you wish to convey?
• What is your USP?
• What is the 20-second summary of your talk? What is the point of it?
• How can you help the audience?
• Why you? Why you giving this talk?
• What anecdotes and pictures can help you achieve these aims?
• How honest dare you be?

Then consider some of these points and these and finally these:

• Decide in advance exactly what your first sentence is going to be. This will remove the umm-ing and ahh-ing that often marks the start of people’s talks. There should not be an awkward gap between being introduced and getting into your stride. Ditto for your closing sentence.
• Open with something that grounds your talk in the “right now”. No waffle.
• Don’t turn round and talk at the screen. Talk to the audience. Glance at your computer if you need to, but you should be comfortable in your head about which slide comes next.
• Remember: you are on the stage because you are an expert. You know more than the audience does. Let that thought help you to relax and be confident.

I hope this was all helpful.

Good luck!