Episode 34: It Gets Easier Each Time
May 26, 2025
Like public speaking or parallel parking, reconnecting takes practice.
Reaching out to people you’ve lost touch with is harder than it should be—until you actually do it. Whether it’s old friends, former colleagues, or connections that quietly faded over time, the first message can feel awkward or even intimidating. But with each attempt, the process gets smoother, more familiar, and surprisingly rewarding. This episode explores why that initial outreach feels so vulnerable, what happens when you push through it, and why re-establishing connection—just like anything else—gets easier every time.
Transcript
i've never been particularly great at staying in touch with people that's probably an
understatement i am really quite bad at staying in touch with people there have been plenty of
relationships in my life that have come and gone friendships and and everything else that have come
and gone and mostly they're they they sort of dissipate because neither myself nor the other
person to be fair but but we just don't put that effort in to routinely touch base depending on how
i look at this it is in some ways easy to look at this and think to myself well
you know was it a real friendship that's probably not fair they are these the you know if you have
a friendship and you know for several years and then you kind of lose touch or whatever
those several years still happened right so it's it's it's not a fair thing to say was it a real
friendship there's always the question mark of well was it a friendship born completely out of
convenience right was it just that it was easy to maintain when you were still physically in a
similar space as i've gotten older and had more a higher quantity of professional relationships
enter into my life the same pattern has occurred where where you know you kind of have a professional
relationship with someone maybe you work together frequently for an extended period of time and then
once that project is over or that you leave that job or they leave that job or whatever that it just sort
of dematerializes so this has always bothered me i don't i don't like losing the those relationships but
on the same token i haven't done anything in particular to grab them back or maintain them or anything else so
it's it's kind of like a you know you get what you give kind of thing so anyway i've been trying to be
better about this or different about this particularly over the last let's call it six to nine months
i've been trying to go out of my way to both touch base with people who i haven't in a long time
and also in cases where maybe i'm in regular contact with someone and then i'm not anymore trying to
maintain that better now i know people who this comes very naturally to where it's just easy uh to to
maintain these things they don't have to think about it for me it it it it's both
it both seems like a lot of work and also it it almost brings with it a certain level of
it's almost nerve-wracking in some ways it takes a certain something out of me to reach out to
someone who i haven't spoken to in you know maybe months or years or could even be longer to reach out to
them and say hey you want to grab a cup of coffee you want to grab a lunch whatever like just the act
of doing that is difficult and and then you get there and you have to kind of you know you know
you're going to make some some small talk with them and discuss old times and it's a whole thing
right what i've found though in doing this is is a couple of things and i thought i'd share them
one thing that i've noticed is that and this probably isn't a surprise to anybody but it's
that initial reach out that's probably the hardest part of all of it that initial reach out of like
hey haven't spoken with you in like 10 years are you still in the area do you want to grab a coffee do
you want to hop on a zoom call and chat like whatever your preferred medium of that sort of
thing is that initial reach out is difficult i'm sure there's a lot of reasons why that's difficult
i'm sure psychologically you know there's there's a almost like a power dynamic thing there
um afraid of you know fear of rejection uh you know all sorts of things but what i've noticed
is that first of all you have to kind of almost get in the mindset of like well i'm just going to
do this and they can you know at that point the ball's in their court they can choose to engage with
this or not i'm not going to be upset about it either way i'm just going to let it shake out from
there but at the very least i've done this much and i can stop thinking about it and i can stop being
like oh you know who i should reach out to so and so another thing that i've noticed is that
oftentimes you know oftentimes it works out just fine going and grabbing a lunch or whatever
and that conversation tends to flow very easily like once you're actually there it's almost like
just being back with old times any anxiety around oh if we get together is it going to be awkward
we're going to need to talk about it we're just going to sit there and stare at each other
i don't think that's founded in most cases i'm sure there are cases where that that can happen but
generally speaking i haven't found a problem with that and by the way i'm not the best at something
like you know just carrying conversation but it it tends both sides have that same idea that same
anxiety around things and it's very but it's i don't think it's founded i think it once you're
actually there and in the moment and all that it kind of just flows easily there are things to talk
about think about it think about it logically you used to share all sorts of things together
whatever those things were friendships professional stuff whatever and then a bunch of time has passed
which means that a whole bunch of events have occurred in the interim which are things that
you don't know about each other in some ways logically it would make more sense that it would
be harder to have a conversation with someone that you see every single day than someone that you haven't
in a long time the final third and final thing that i want to say on this like sort of what i've
learned along the way here i liken this very much to other things that might bring along with them
certain anxiety for example i'm not saying that all these apply to me or apply to you or anything
else but just some examples of things that often do that it's similar to presenting in front of people
it's similar in uh similar to doing networking events it's similar to any of these things that are very
often pointed at as things that people have anxieties or phobias around the more you do it the easier it gets
and i think this is the main thing that i've taken away from really uh a much more concerted effort
over the last well actually we'll call it nine to twelve months of just trying to do more of this
sort of stuff more social more intentional socialization it gets easier every time the first
time that you reach out to someone who you haven't spoken with in five years is kind of nerve-wracking
and then but the next time you do it you will have at least had one practice round in you
and the third time you do it and the fourth time you do it the fifth time you do it every single time
it almost becomes practiced you can kind of go to the same group of of uh fallbacks or lines or
however you want to look at it in cases where you get stalled out or you're not sure what to say or
whatever each time you do it it will get a little bit more fluent and easy and practiced and in a case
where you're doing something i'm not suggesting that you know friendships and and relationships
should be practiced right but in that case we've got to get back into the swing of something
in the case where you have an anxiety around something having a little bit of practice under
your belt having those fallback kind of mechanisms and methods goes a long way towards being able to
ease any um issues there or or ease any you know tenuous feelings so i gotta say that for me
having done quite a bit of this recently it's quite i've found it quite um rewarding and like an
important thing that i'm very glad that i have more intentionally been doing this as of late
if there's anyone for you that you haven't talked to in a while and you just always think to yourself
in the back of your head oh you know i should really reach out to somebody just do it reach
out find you know we are surrounded these days with with messaging platforms i'm sure you can get
a hold of them on one of them text them dm them linkedin them like whatever like whatever it is
that that you wherever you know they are reach out and and maybe they're not you know some of these
cases i've reached out we've had lunch once and then that was it in other cases now i'm in regular
contact with another person and and that social contact is is uh very important things particularly
in today's world so i would encourage you if if any of this sounds familiar to you just just give
it a whirl just just just try it maybe make yourself a list make yourself a list of the of three to
five people you haven't reached out to in a while and and just you know once a week reach out to
somebody else you'll be surprised how more fluently and naturally it comes each time you do it