Future Work/Life is a regular newsletter in which I share ideas, bring you interesting stories and articles, analyse industry trends and offer tips on designing a better work/life. If you enjoy reading it, please share it!
As the deadline to submit the manuscript for my book, Work/Life Flywheel, approaches and time is even tighter than usual, I’ll be varying the cadence of the newsletter. Instead of once a week, it may be once every ten days, or even once every fortnight. Frankly, whenever I have the time to share something I think you’ll find interesting, I will! For the same reason, there’s no Any Other Business Today, but during what’s a difficult time for so many, I thought I’d share a selection from the archives that offer reasons for hope and should bring a smile to your face:
Christine Armstrong - Making Work Better
Rory Sutherland - The Future of Work, Offices and Cities
Shaun Tomson: Purpose and Flow in Surfing, Work and Life
If you're anything like most of the people I've spoken to over the past year, you're contemplating making a change in your work/life. Whether you're thinking about changing jobs, starting a new business, or just setting more time aside for that hobby you'd abandoned, I can confirm that we're in the middle of the greatest work/life transition ever.
The change you're envisaging will, no doubt, be different from that of your partner, friend, colleague, or boss. At this point, it may still feel more like a dream than a reality, as you wistfully contemplate replacing a sense of mundanity with doing something you love. You may have dipped your toe in the water by starting a side project or moonlighting outside (or shh, during) working hours. Or if you’re particularly bold you may even have taken the plunge and quit your job. However, the chances are, although you've already decided you’ve worked one day too many securing someone else's future, you haven't yet mustered up the courage to act.
Don't worry. You're not alone. The reality is that, particularly when it comes to going it alone, many people want to do it, far fewer follow through.
Why?
Invariably, it comes down to fear of failure, which isn't a surprise when discussions about pivoting your career tend to focus on the risks - some real and some perceived.
Suppose you're like me and have a mortgage and young children. You may be wondering how the financials of your new career direction stack up against the security of your employment contract and steady income. If it doesn't work, how will you pay the bills?
How about the fact you've never done it before? If you've only ever worked for someone else, how will you know where to start when it comes to all the tasks unrelated to your skillset. If you're a marketer, what do you know about running payroll? Running a digital marketing campaign may seem like a mystery if you work in finance, and if you're a designer, where do you start when it comes to trying to win new clients?
The final reason that most frequently comes up in my research is reputational risk. What if it doesn’t work out and I look like an idiot? What will people think of me if I don't get it right? How will I look at myself in the mirror if I quit my successful job and try something that fails?
Ok, so I get all that. There are always reasons not to do something. The thing is, there's an even bigger reason to take the chance, but to see it, we have to cast our minds into the future and look at our choice through the lens of regret. Quite simply, in your short and long-term future, you're far more likely to be satisfied with your decisions after demonstrating the courage to pursue your ambitions. Or, to put it another way, you're more likely to regret inaction than action.
In Daniel Pink's research for his new book, The Power of Regret, he ran a global survey asking people to share their greatest regret. Among the nearly twenty thousand people who contributed, the overwhelming wish looking back was that they'd adopted more of a bias for action and the greater the time that passes, the more profound the sense of regret they experienced when they didn’t.
As Dan explained to me on the Future Work/Life podcast last week, people very often rue their failure to act boldly in their work and personal lives. As one of four key types of regret we experience - the others being foundational, moral and maintaining connections - boldness regrets, in particular, grow stronger over time. Looking back in twenty years, our negative feelings towards our lack of action into starting something new,mo will only get stronger.
"We have a very good sense of what future you is going to regret. Future you is not going to regret buying a blue car over a grey car. The you of five years from now is not going to regret wearing a green sweater today or a blue sweater today. That's just not going to be significant. What future you is going to regret, if we believe these seventeen or eighteen thousand people who have submitted their regrets, is not building a stable foundation for your life. Future you is going to regret not taking an appropriate risk. Future you is going to regret not doing the right thing and future you is going to regret building connections to people you love. And that's it."
It turns out that failing to be bold is far riskier in the long run than failing in a new venture.
As a thought exercise, imagine yourself twenty years in the future looking back on the decisions you make now. How would you feel if you didn't follow through when you're confident in your abilities, knowledge, and capacity to learn? Back in the present, this 'what if?' question elicits the same insights every time: most people wish they'd spoken up more, made the jump into going it alone, and set up their own business.
There's also value and learning to be had in confronting regrets about decisions we’ve already made. Understanding our emotions teaches us lessons about ourselves and how to make better decisions in the future. During our conversation, Dan broke down how the scientific literature has successfully demonstrated a systematic way of doing this by following three distinct phases – what he calls inward, outward, and forward.
You can read part two of this article in next week’s newsletter. Until then, have a great week!
Ollie
You can listen to my conversation with Dan, HERE.
In this week’s podcast I speak to Cleo Sham, Partner at Stride the UK-based early-stage venture capital firm.
Before joining Stride in 2021, Cleo's illustrious career took her from McKinsey to Merrill Lynch before becoming General Manager of Uber in China. She scaled the business from 3000 to 4 million weekly trips and $700 million in revenue. She subsequently ran Uber's ridesharing business in EMEA before moving to Spotahome, a Series-B stage prop-tech marketplace. After two years there, she took a much-deserved sabbatical before jumping from operator to investor at Stride.
We had a great conversation in which we talked about managing stress and burnout in start-ups, the most exciting themes she sees in workforce tech, transferrable skills for people pivoting their careers, and the importance of creativity for founders and investors.
You can listen to my conversation with Cleo, HERE.
