Ever Feel Like Your Career Is a Failure?

How to Reframe Career Failures as Valuable Learnings

Oct 16, 2024

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.

My Career Failure Story

Career Preparation, 2004-2009

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.

Military Career, 2009-2014

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.

Startup Career, 2014-2019

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.

Portfolio Career, 2019-Present

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…

To Be Continued...

So, you see, I’ve had more than a few setbacks and missteps in my career so far. But I’ve learnt so much that I really have nothing to regret, at least when I’m thinking rationally. If I keep this up, working to retirement age, I have another six mini-careers to come. That’s exciting, and it encourages me to think big and take calculated risks. I’ve just started studying for a personal trainer qualification, I’m planning to volunteer for the local search and rescue team, and I’m researching humanitarian aid work.

Next time you worry you’ve not achieved more, pause and reflect. Ask yourself not what you’ve achieved in your career, but what have you learnt? If you can look back and honestly say you consistently showed up, did your best, and learnt from your failures and struggles, you’ve already achieved something to be proud of.

You may want to keep your learnings to yourself. You may wish to share them for others to learn from. Either way, I guarantee you’ll find this exercise cathartic and enlightening. It certainly helped me let some bad stuff go, relearn some important lessons, and celebrate some career highlights I’d long since forgotten about.

Career Failure Story Exercise

What are your career failures? If you’ve never really thought about it, or even if you have, I recommend you write a candid history to draw them out and process them:

Allow yourself 30 minutes in a comfortable environment with no distractions.
Divide your career into multi-year chapters, split by role, company or time period.
Relive your experience, writing in stream of consciousness style, in the first-person present-tense, one chapter at a time. Don’t worry about accuracy or style.
Focus on your experience, how you think about your achievements and, crucially, your perceived failures. What did you and didn’t you enjoy? How did you feel?
Take a break, reflect on what you wrote, come back and add detail as necessary; reflect some more, write some more, repeat. Resist the temptation to edit yourself.

Let’s Finish on a High!

I don’t think it’s helpful to dwell on negatives so, next week, I’ll share a template to write the Hollywood version – your Career Hero Story. Having written a cathartic career history focused on the negatives, the positive version will enable you to reframe your failures as learnings and portray yourself in the best possible light to land your dream job or win work. If you need support in the meantime, members are welcome to reach out to me personally. Please share your story and ask for feedback.

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.