Who am I when I’m no longer working every day? Am I still a professional if I’ve retired from my job? What’s my purpose now? What will I do with all that free time?These vexing questions hit too many of us only when we’re on the cusp of that dirty R-word: retirement. We spend decades planning our “Third Act” financially but forget about the mental, emotional and relationship aspects of this huge change in our lives.Every year thousands of executives and workers finish up long and successful careers but few are prepared for what’s next. Too often I hear, “Oh, my partner is looking after that”, when I ask chief executives, founders and senior executives about their retirement plans during succession coaching sessions. When I speak to the person’s other half, inevitably they say that beyond the finances, some mention of golf, tennis or hillwalking and a bit of travel, it’s never been discussed.Incredibly, these high performers – who are crafting corporate strategies, developing market entry plans, growing effective leadership teams and influencing stakeholders – are leaving happiness in their third act to chance. Why?Retirement is no longer a hard stop on a 40-year working life. It’s the beginning of another active phase of life, not an end to all work and play. Chances are, many of us will live into our 90s and even to 100 so we need to work towards a viable strategy.Studies show people are most satisfied in retirement when they have planned ahead to ensure they have enough money, good physical fitness and a supportive, aligned partnership, but least happy when they’ve failed to build strong social networks or psychological resources.[ Money and health the big concerns as living to 100 becomes a reality, new survey showsOpens in new window ]This later phase in our working life is fascinating and underexplored. For the past year, I’ve been interviewing Ireland’s top leaders about their third-age journey, especially about what worked, what didn’t and when they started to think about it. Many excel in this life stage, reinvigorated by a new sense of purpose in their community and family, a less structured work day and more time for physical activity. For some, though, a failure to design the future, or a flippancy about all it entails, led to a more difficult journey than necessary.To gather more stories on this topic – and to help people use a playful approach to this next phase – I’ll be hosting a webinar for the Institute of Directors called Designing Your Third Act and asking you to email me your insights.Designing happinessRetirement is rarely an ending, it’s just an underdesigned beginning. And we can design it for happiness, joy and even delight. Our lives can often be the fulfilment of others’ expectations, not necessarily our own. Parents often decide on our schooling and, in some cases, they steer us into our careers too. Sometimes retirement is the first time we ever ask ourselves: What do I want? What makes me happy? Who was I before work, partnership and children?These are big questions without easy answers but a return to the playfulness and experimentation of our youth can help us find solutions years before we actually retire. Instead of treating retirement as a problem solved only by hitting a big pension number, why not use playful learning techniques and little experiments to bring your next phase into focus? Over the past few years I’ve tried the following techniques: design thinking principles, Lego Serious Play methodologies, drawing exercises and card games, so that the third age – which for me is five to 10 years away – becomes a fun and interactive personal challenge explored with curiosity.My personal experiments over the past five years have included learning to sail and getting my international skipper’s licence, weekly date nights with my husband, playing the Chinese tile game Mahjong weekly with new friends, trying padel and pickleball, getting a monthly deep tissue massage, travelling by canal boat to see art exhibitions and ancient cities, setting up a weekly sea swim and sauna group with my girlfriends and spending a month or more abroad with my husband each year. Before this playful period, I didn’t think we had time for all this self-indulgent foolishness. We were busy working full-time, minding the kids and managing the household: who had time to dream or plan for the future?When you’re curious, you treat retirement as an open question rather than a fixed identity you have to defendNeither of us has any plans to retire soon – or limitless funds – but these little tests are wonderful experiences together and they show us individually what energises us and what drains us. It has also made us more intentional in our life choices, especially who we spend time with and what we do together each day, week, month and year. Now that our children are starting their careers and travel adventures, we know our plans will need to be flexible based on their life decisions, too.A time of renewalOne theme appears consistently in the research, interviews and coaching: relationships. This might mean a partner, children, older relatives and friends, both old and new. How are you aligning your life to make sure that in your current career situation, you have the best chance of maintaining good personal relationships and long-term health? Do you need to make some changes?Maurice Pratt, the well-known businessman, told me that he tells friends and colleagues there are two questions you should never, ever ask your partner when you retire: “what are we having for lunch?” and “where are you going?”To avoid these disasters, I try to help clients develop five mindsets based on the Designing Your Life framework of Stanford University’s Bill Burnett and Dave Evans: curiosity, action, reframing, awareness and radical collaboration.Curiosity. When you’re curious, you treat retirement as an open question rather than a fixed identity you have to defend. The goal is shifting from “Who am I if I am not my job?” to “What else can I discover about myself?”Bias to action. This shows up when you prototype small experiences before committing to large, irreversible life decisions. For example, you can commit to trying a two-week volunteer stint at the local animal shelter before committing to a two-year board position. Test your assumptions in the real world with low risk.Reframing. In coaching, we talk about limiting or dysfunctional beliefs. When you name and dismantle personal, relational and systemic obstacles (fear, identity loss, finances, health, family expectations), you free yourself up for new experiences. Changing your thoughts from “It’s too late to start something new” to “I have a blank canvas to design my next chapter” gives you more energy for fun experiments.Awareness. Develop a way to track your energy and engagement daily. That might be through journalling, taking notes on your phone or using an app. Two minutes reflecting on your day helps show you what activities and environments actually give you life versus what drains you.Radical collaboration. Although we live on an island, we are not alone on an island. At work you’ve relied on your colleagues. Now you need to lean on your family, friends and community. Other people’s perspectives and working together on activities helps you recognise that you don’t design your life alone; great ideas often come from collaborative brainstorming.Margaret E Ward is chief executive of Clear Eye, a leadership consultancy. margaret@cleareye.ie