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How to Reconnect Like No Time Has Passed (Even When it Has)
Picking back up with someone can feel awkward if a lot of time has passed—but it doesn’t have to.

Read time: 5 minutes
Hi Proactive Professional,
If we’ve dedicated all of this time and energy to building better connections, how did we get to the point of needing to reconnect at all?
Well, life is busy, and it only gets busier with time. We get new jobs, new priorities, new partners, new responsibilities, new hobbies and much more. In whatever new chaotic life stage we enter, we tend to prioritize staying afloat with everything that's on our plates at the moment rather than keeping up with those special people from the prior life stage:
The friends that moved to new cities
The old coworkers you no longer see daily
The hobby where you saw people regularly but no longer have time for
And from each of those groups, we've said the same infamous phrase "We're going to keep in touch!" But as we move cities, switch jobs, and change hobbies, we quickly begin to lose touch. We let more and more time go by without reaching out, excusing ourselves by saying “we’re just so busy.”

Don’t let this much time pass…
It turns out, everyone experiences some version of this. There is simply no replacement for the role that proximity or seeing people regularly in a "third place" plays in relationships: living nearby them, seeing them each week at a hobby, or interacting daily at work.
We can't recreate that when we are no longer in that place. It doesn't make sense to call every day or make regular small talk when they are no longer part of your routine. But it also doesn’t make sense to let years go by with nothing more than a few social media likes, comments, and happy birthdays exchanged between you two, either.
Where is the middle ground?…Reconnecting.
But why does it feel so difficult?
I think about it like this: With each day that passes you lose a bit of mutuality, until you get to the point where it feels like there is none left.
You start to overthink things: What if they are a completely different person? What would we even talk about? Do they even want to hear from me? I told them I'd keep in touch but it's been an embarrassingly long time. I saw they moved jobs and cities so where would we even start the conversation?
With so many potential changes, it becomes overwhelming to know what to say and when to say it.
Well, I’ll let you in on a little secret….you're looking at it wrong.
Nothing changes the experience you had with that person. Not the amount of time that goes by, not the career changes, the places they’ve moved, the hobbies they’ve dropped or picked up, or any other major life events that have transpired.
Take it from someone who has made some drastic career changes in the past seven years. I started out in healthcare only advisory for companies selling to other companies, then moved to buying companies in all industries except for healthcare, then shifted to a strategy role at a niche aviation company, and finally started working in the connectivity space.
When I think back to the mentors and colleagues I had at the first healthcare advisory role (many of which are still in that space), I don't feel like I have any mutuality at all to reconnect on.
But instead of hoping there are some remnants of common ground we can connect on, I look at reconnecting as a way to show gratitude for that part of our lives when we were closer and reconnect relearn about who they are now.
How to Make Reconnecting Easier:
1. Acknowledge Any Awkwardness
There is no harm in calling out how long it’s been in a lighthearted manner. If you feel that it’s been way too long, they probably feel similarly (and may even be a bit embarrassed about it themselves). By acknowledging it, you are labeling the elephant in the room and diffusing any awkwardness or tension about it.
A simple “It’s been way too long, and that’s on me…” goes a lot further than you’d expect.
(p.s. labeling is a technique backed by behavioral science and often used to diffuse negative emotions and promote positive emotions. I first learned about it from former FBI negotiator, Chris Voss, in his book: Never Split the Difference: summary here)
2. Share Your Appreciation
Show Gratitude: This could look like telling them how they’ve helped you and the impact it had or just showing gratitude for some of their qualities that made you enjoy any time spent with them. It often comes in the form of gratitude for advice, friendship, mentorship, or them being there for you.
Show you were thinking of them: It could be about a sport, an inside joke you used to have, or anything that reminded you of them. People appreciate when others think of them. Make sure to mention it.
For professional connections you may mention “It always impressed me how you handled X…”
While personal connections can be as simple as “I was thinking about that funny time we…”
3. Make it Easy to Respond
The biggest mistake you can make when reconnecting after a long time is asking “So, how have you been?” This is a cop out of a question and puts all the effort on whoever is receiving it. Should they talk about the last two career changes, new move, house they bought, pets they adopted, or tough time they just went through? They’ll probably answer with a bland “everything is good!”
It’s your job to be more specific than that. Try picking one thing to ask them about. If you saw they made a big career change: “What led you to the big switch.” If you used to share a hobby with them, “Are you still playing soccer or did the pickleball craze get you too?”
Don’t worry, I guarantee a conversation starting in one place will cover many more things going on in their lives right now.
4. Give a Reason for Reconnecting
Don’t beat around the bush. Mention if you’d like to catch up over the phone, hang out soon, get their perspective on something going on, or just generally be a bigger part of each other's lives. That’s where the real reconnecting and relearning begins to take place.
The relationships you have with others are in constant flux. People who were once part of your routine may now live far away and others you’re just meeting could become important parts of your daily life.
But that doesn’t mean we should let certain connections drift away completely. When we start to make that mistake, it’s important to reconnect. It doesn’t have to feel like some impossible task if you take this thoughtful approach.

What I’m committing to this week for building relationships:
⚽ Co-hosting Pitch on the Pitch: Soccer Networking for Tech, on Thursday at 7pm ET. Sign up on Luma or Conquer! (~2 hours)
🤝 Meeting other founders and builders in the connectivity space hosted by a super connector (~2 hours)
📞 Chatting with two founders building companies in the gratitude space (~1 hour)
🍽 Meeting up with a former colleague for lunch (~1 hour)
🤔 Reflecting on my week this Friday: Who are three people I’m due to reconnect with? (~15 minutes)
What are you committing to this week? Reply to this email!
Helpful links:
Best of luck building,
Devin