Thinking About What’s Next · Post 9 of 10
You cannot do this alone. And you don’t have to.
There’s a particular loneliness that comes with this stage.
You’re thinking about things that most people around you aren’t thinking about yet. Your colleagues are still climbing. Your friends are busy. Your family wants you to be okay. And so you carry the question quietly — not wanting to seem ungrateful, or restless, or vague — while it gets heavier.
What you’re missing is not therapy, or a coach, or a plan. (Those things help, but they’re not the first thing.)
What you’re missing is people who get it.
What the research says about social support in transitions
Research on career transitions in midlife consistently identifies social support as one of the strongest predictors of successful navigation — not just emotionally, but practically. People who have at least one person who truly understands what they’re working through show lower anxiety, higher follow-through, and better outcomes.
This is not about cheerleaders. Cheerleaders say “you can do it!” and move on. What you need are people who will sit with the complexity, ask the harder questions, and tell you the truth when you’re rationalising.
Two kinds of people you need in your corner
Your Sounding Board — the two or three people you trust completely to be honest with you. They’re not just your support network; they’re your calibration mechanism. They know you well enough to see your blind spots, and they care enough to name them.
Not everyone in your life qualifies. Choose carefully. Your Sounding Board is not about who likes you most. It’s about who sees you most clearly.
Your parallel travellers — people who are in a similar season of life. Not necessarily further ahead, not necessarily further behind. Just navigating the same territory at the same time.
These conversations are different from the ones you have with people who’ve already figured it out. There’s no performance required. You’re all still working it out.
Finding your parallel travellers in Singapore
The Mid-Career Pathways Office (MCPO) runs regular workshops and peer sessions for professionals in transition. The National Volunteer and Philanthropy Centre (NVPC) connects mid-career professionals with meaningful contribution opportunities — a useful way to find people driven by similar values. LinkedIn communities, alumni networks, and coaching peer groups are others worth exploring.
But honestly? Some of the most useful tribes start with one honest conversation. One person who says, “I’ve been thinking about the same thing.” And then you meet for kopi, and it becomes a standing thing.
What we heard from people who found theirs
One person we spoke with described how his own informal tribe — the board game community he and his partner had quietly built — had become something far more significant than a hobby:
“We try to meet different friends at least once every other month. Not always the same people. Board games, yes, but we also talk, catch up. We’re building something — social bonds that will matter when we are older and need people around us.”
— CH, age 59
He wasn’t describing a networking strategy. He was describing something he’d built slowly and intentionally, over years, without knowing how important it would become.
Another described what happened when she finally had a space to think out loud:
“This conversation — your prompts — allowed me to bring things to the surface that I’d had at the back of my mind for weeks. I hadn’t realised how much I needed to actually say it out loud.”
— BL, 45
The insight wasn’t in a book or a worksheet. It was in the conversation.
An honest note on community
Building a tribe takes time and some vulnerability. You have to be willing to say “I’m not sure what’s next” to people who might not say the same back. You have to be willing to not have answers.
This is harder than it sounds in Singapore’s culture, where certainty is often signalled as competence. The people who get through the discomfort fastest are not the ones with the clearest plans. They’re the ones with the most honest conversations.
One action
Identify one person — just one — who you think might be sitting with similar questions. Not someone who has all the answers. Someone who might be in the same chapter.
Message them this week. Not with a plan. Just with a question:
“Hey, are you at all thinking about what’s next for you? I’ve been sitting with that question and I’d love to compare notes sometime.”
That’s it. That’s how a tribe starts.
Post 9 of 10 · Thinking About What’s Next
← Post 8: You Don’t Rise to Your Dreams. You Fall to Your Systems.
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