Be The Hero of Your Career!
How to Tell a Confident & Compelling Career Story
In my last post, I shared my Career Failure Story and showed you how to write yours. Now I’m going to show you how to write a compelling hero story, so you can convey your value clearly and confidently to hiring managers, recruiters and your network.
Recapping The Career Failure Story
Whether you’re mid-career like me, 50 and peaking, or an ambitious 20-something, you’ve probably experienced self-doubt about your career. It happens to me all the time, and to most people if they’re being honest. Many struggles and failures, and much effort, are hidden beneath the surface of an impressive CV or LinkedIn profile.
When insecurity creeps in, I try to reframe things. Not: what have I achieved in my career? Rather: what have I learnt from my career? It’s important to remember every experience is a learning opportunity, whether it’s a “success” or a “failure”.
On reflection, since I’ve been old enough to choose, I’ve lived life five years at a time. Below is what I learnt from the first twenty years of my career – full disclosure, warts and all. I found it enlightening writing a history of my career; perhaps you will too.
On to The Hero Story
Having shown you the failure version – or “loser story” as one mentee put it! – based on the doubts that creep in when I’m struggling, I’m now sharing the hero version. Note that the facts remain the same: there’s nothing untruthful about this positive version, nor even any embellishment; the difference is a shift in focus and perspective. I’ve put the two versions next to each other, so you can easily compare.
My Career Hero Story
Career Preparation, 2004-2009
Failure version:
Last year of school, focus solely on getting grades I need for uni, stress a lot. Turn up at Oxford shy and awkward, having spent teens studying and playing guitar in my band. Don’t love literature-heavy content of course. Drink far too much to cope, learn some hard social lessons. Make great friends but feel inadequate surrounded by high achievers. Push myself to take up rowing, ambitious choice of sport for a non-athlete! Start in college’s 2nd boat, cough up lungs twice daily, we lose every race for a year. Offer to sub into 1st boat when they need, finally asked to join, made vice-captain. Weakest guy in crew, chosen because I’m consistent and technically sound, we do OK. Live in Russia through winter. Intern as translator in Paris, not very well. Final year, quit rowing to focus on exams, regret it, get respectable 2:1, no idea what to do with it. Find confidence, revisit boyhood dream to join Royal Marines, eyesight too poor but just good enough for British Army.
Hero version:
It’s my final year of school, I study hard and achieve my dream of getting into Oxford University. I arrive at Oxford wide-eyed and eager to develop myself: mentally, physically and socially. My course is challenging and I learn quickly in the supportive environment. I throw myself into socialising and make great friends, who encourage me to grow as a person. Determined to prove myself, I join the college rowing club; my novice crew trains twice a day and is racing within weeks. Keen to push myself, I volunteer as a substitute for the 1st boat. The following year, I earn a permanent seat and am elected club vice-captain. I’m not the most powerful oarsman, but I’m technically capable and I help the crew to a respectable ranking. I spend a winter in Russia, immersing myself in the local culture, followed by a few months as an intern translator in Paris. I love my travels although decide not to pursue a career in languages. In my final year, I take a more disciplined approach to studying and explore some alternative activities beyond rowing; including the Officers’ Training Corps, which inspires me to revisit my boyhood dream of joining the military. I apply to become a British Army officer.
Military Career, 2009-2014
Failure version:
Selected for Army officer training. Backpack across Central America. Move back with parents. Assemble miners’ lamps in Dad’s factory, run, deliver Domino’s pizzas, lift weights, repeat for a year. Road trip through California. Hike across Corsica. Attend Royal Military Academy Sandhurst for a year, struggle mentally, pass OK. Attend infantry training in Wales, instructors tough, carrying injury, struggle through. Brief respite of fun training in Dorset, perform well. Soul-destroying training in Canada, perform poorly, think about quitting. More enjoyable training in UK, perform OK. Cut from Afghanistan deployment last minute, for political reasons, devastated beyond belief. Eventually deploy as reserve, command 50 soldiers in armoured vehicles, best performance to date, career highlight. Back to Wiltshire, promote, responsible for 150 soldiers’ training, challenging but unexciting. Resign commission, sent to Wales to run training course, dread it, feel like I’ve been exiled because I have one foot out of the door.
Hero version:
Having been selected to train at the Royal Military Academy Sandhurst, and having not taken a gap year between school and university, I defer my place and go on some adventures before life gets too serious: backpacking through Central America, road tripping across California, and trekking the mountains of Corsica; funded by working in the family miners’ lamp business and delivering pizzas for Domino’s. My physical training for Sandhurst pays off, and although the culture shock is significant I perform pretty well. I take the calculated risk of putting all my eggs in one basket, and ultimately earn a place at my chosen regiment. Infantry training in Wales is the most physically and emotionally testing thing I’ve ever done. I fight through shin splints and ultimately pass a very tough course. The armoured vehicle courses that follow are more mentally challenging in some respects, but in a relaxed and social environment. Having joined my unit, I’m thrown almost straight into complex overseas training in Canada. My inexperience shows, as the greenest officer, but I get back on track once we start preparing for Afghanistan. After months of training, due to the government reducing troop numbers, my company doesn’t deploy. This is a setback, but I stay prepared and get my chance several months later when a colleague has to return home for a new job. I take command of a platoon in a spartan patrol base in Helmand Province, participate in fulfilling counter-insurgency missions in a fascinating country, and am fortunate to bring my soldiers home in one piece – it’s the pinnacle of my military career. Back in the UK, I’m promoted to captain and become a chief of staff in barracks; I’m responsible for the training and deployment of 150 troops, which although interesting lacks the excitement of operations. Having resigned my commission to seek a more cutting edge opportunity in the civilian world, my final task is to help run a promotional course in Wales; I enjoy the responsibility and feel vindicated for past failings.
Startup Career, 2014-2019
Failure version:
Move to London with no job. Apply to work at Deliveroo, have no real commercial experience, get rejected. Help my brother with his pre-revenue business, teach myself everything, burn through my savings. Apply for ops manager role at Deliveroo, hired as employee number 15ish, don't yet understand my value, start at half my previous salary. Culture shock, drink 6 double espressos a day, always on. Negotiate share options and pay rise, promoted twice in 2 years, build and lead a team of 80. Moved out of beloved ops department in shock restructure, boss and mentor sent to Hong Kong. Consider leaving, instead take opportunity to run projects across 13 countries for 300 employees and 60,000 couriers. Experiment with electric vehicles and micro-mobility solutions, can’t make anything stick long term. Culture turns corporate, big hitters hired from outside for senior roles, reach promotion ceiling. Ultimately help grow ops 500x in 5 years before leaving.
Hero version:
Having left the Army, I move to London undecided on my next job. I apply for a regional expansion role at Deliveroo, whose simple proposition speaks to me, and interview with founder Will Shu himself; however, it’s not quite the right fit because they need someone to sell. While interviewing with various startups, I start to develop my commercial acumen; and I learn to build websites, helping my brother establish a foundation for his private tutoring business. A couple of months later, I see an operations manager vacancy at Deliveroo and jump at it. The MD and Head of Ops are impressed by my tenacious self-development efforts. Within days, I’m employee number 15 and the second ops guy at what turns out to be the fastest-growing startup in Europe. I work hard to pass my probation and receive a significant pay rise with some equity. I’m promoted to assume leadership of London operations, grow the team to scale from 100 to 3,000 couriers, then am promoted again to build a central operations team of 80 office staff serving 20,000 couriers across the UK and Ireland. Following a restructure, I move to the global operations team and become an internal consultant on operational best practice for emerging markets like France, Dubai and Singapore. Lastly, I take the opportunity to work for the CEO and COO on special projects affecting 60,000 couriers across 13 countries; including enhancing rider community, and launching industry-first pilot schemes renting flexible e-mopeds and ebikes to couriers.
Portfolio Career, 2019-Present
Failure version:
Quit Deliveroo, backpack across South East Asia. Road trip from UK to Portugal and back, go over budget, need cash quickly, start freelancing. Move to Antigua with few savings. Go into business with local company, choose wrong product, can’t align with owner, venture fails. Pandemic hits, nearly out of money, visa delayed, consider retreating to UK. Quickly pivot, double down on remote freelancing, win UK contract. Deliveroo IPO tanks. Start making money, win more UK business through referrals. Pandemic worsens, business slows, best UK client folds. Antiguan economy crippled, 18 month curfew, lose only local client. Several UK clients come through at once, nothing for months, repeat. Second local venture falls through. Shift from consulting to mentoring, invest thousands in marketing, get little return. Get great testimonials, build book of repeat UK clients. Global economy tanks, cost of living rises. Still testing and adjusting portfolio career…
Hero version:
As growth settles down and Deliveroo begins gearing up for IPO, I feel it’s a good juncture for me to try two things I’ve dreamed about: being my own boss and living abroad. I take a few months off to backpack across stunning South East Asia and road trip from the UK to the wild West Algarve, reflecting on my career and potential next steps as I go. I decide to take a punt and move to Antigua, hoping to launch an EV joint venture. Six months later, the pandemic blows that and other local business ideas out of the water. To make an income, I quickly reinvent myself as an operations consultant; drawing on my London startup network, and with a strong personal brand, I secure my first client. Business development isn’t my forte, but I deliver quality work and get a steady stream of mainly UK-based clients through direct referrals and word of mouth. I explore other local ventures; however, in a tough economy it’s more sensible to double down on remote work. Avoiding the small business feast and famine cycle isn’t easy, but over time I learn what I enjoy most and am therefore best at selling – mentoring. I get a lot of satisfaction from helping early stage founders establish and scale their business and, when the job market turns due to the economic slump, I discover an additional opportunity to help startup and scaleup employees develop their career, service people transition out of the military, and job hunters land much-needed work.
My Future Career
My business is growing and changing. I’m building out my portfolio to incorporate more hands-on work, potentially humanitarian aid and search and rescue, for camaraderie and the more visceral challenge I miss from my military service; and also because, given the privilege I’ve enjoyed in my own life, I want to give back to those less fortunate. There’s much more I want to do, and I’ll never say never to working for someone else, but for now the flexibility and variety are hard to beat. I get to serve people every day, and hone my skills, and I get paid for it.
Spot The Difference?
Who would you rather hire, or engage as a mentor? Both versions of the story are factual and about me, but the hero version is so much more confident and compelling.
What I’ve observed, especially in my career mentoring work, is many of us compare our failure story with other people’s hero story. Think about that. If you compare the version of your career based on insecurities and perceived failures, to the positive version someone else presents of their career – with all the failures and self-doubt stripped out – you’re guaranteed to feel like an imposter. This will hold you back as an employee, as a candidate, or as a business owner trying to sell your services.
The more you practice telling your hero story, the more comfortable you’ll feel presenting your skills, experiences and positive attributes in a hiring or selling process. Your story will become the basis for your CV summary, your LinkedIn About section, cover letters, application and interview question answers, and more.
Go on, have a crack – I dare you!
Career Hero Story Exercise
Where did you start from? How did you get to where you are now? What’s your vision? Write a hero story about your career achievements and desired happy ending:
Allow yourself 30 minutes in a comfortable environment with no distractions.
Re-read your Career Failures Story and duplicate the chapter structure .
Imagine yourself as the hero of that story, the protagonist of a novel or the leading role in a blockbuster film.
Rewrite your story, in a your own style, by chapter or scenes, highlighting your successes and reframing your failures as challenges you overcame.
Focus on the value you add, what you learn, how good and competent you are.
Tell your story all the way to the end, with the closing chapter being you landing and starting your dream job – or at least the next job you’re targeting.
Take a break, reflect on your story, write more, reflect more, repeat. Edit yourself only to make the story more positive and compelling for the audience.
If you’re still unsure of your career destination, try writing multiple closing scenes.
There’s Power in Sharing
Once you’ve written your career failure story, writing your career hero story will help you reframe your failures and strengthen your personal brand. If you need support, members are welcome to reach out, share your story and ask me for pointers.
I also recommend you discuss your story and learnings with your peers in the chat. It’s amazing how powerful it is to put it out there, to hear how impressed and interested others are by what you consider an ordinary and unremarkable career path.
What Benefits Do Community Members Get?
If you’re interested in joining a community of like-minded peers, and maybe even getting affordable personal support with your career, learn more here.
Love this Paul, couldn’t agree more.
Love this Paul! It was great both learning more about your story and seeing how the subtle, yet effective reframes can make such a huge difference to the self-talk we have. Keep 'em coming 👊🏼