To ask or not to ask - that is the question (or how your impostor syndrome is messing with your brain)

Recently, I read a newsletter from someone I have a lot of respect for, discussing how they've "blown" a really good potential connection that they'd made. I rarely cringe as much as I did when I was reading, but the reason was all wrong.

The writer, a successful business person whose name I am omitting on purpose (like I said - I have a lot of respect for them, and this is going to be a critique), listed all the things they felt they did wrong. How they reached out too fast, how they probably seemed too eager, even rapacious. How they, too, noticed that often, they just keep getting questions and requests.

And on some level, I get it. For a small business owner like myself, and for many (especially women) small business owners, the last few years have been particularly hard. I have both experienced and heard from others about how often they are contacted with request for free work (which, unfortunately, doesn't pay the bills). How people try to squeeze more freebies out of them, and how they may react very negatively when they are told that, strangely, the person expects to make money through their work. I have had more negative responses, manipulations and degrading comments than I care to name, mostly from people who were hoping to bully me into becoming their go-to free work dispenser. So I really do understand the feeling, even paranoia, that others may only be interested in what you can do for them.

But on the other hand, there is the impostor syndrome. Within that newsletter, it was almost palpable, and that's not odd...many of us, and women and minority members especially (but not solely), experience immense amounts of impostor syndrome. The symptoms were all there - a perfectionist who projected their feelings of trespassing past what they "should" be able to accomplish onto another person; feelings that their perceived inadequacy, both socially and professionally, would surely lead to disdain and feelings of being used. There was no interaction with that great contact that would solidly give a reason that, yes, that other person felt under attack somehow by way too much eagerness way too quickly. Predominantly, there were assumptions about cause and effect, joined with how the writer themselves feels about being contacted.

I read and I couldn't help thinking - is that how this person sees interactions then? How do they see kindly occasional social pokes such as kind wishes for yearly celebrations? Do they read them and expect that behind them is some hungry piranha just waiting to pounce? Do they really mean anything positive they say, or do they just know what to say to keep an interest (and a very successful) business going? Are the readers numbers to be added up? Is there anything genuine about them wanting to supposedly share their knowledge? How much is it an introvert with impostor syndrome trying to survive in the world of extroverts who may have the same impostor syndrome but who do not express it the same way?

As you can imagine, this was probably not the intended message of the newsletter. But the fun thing about intended messages and internalised issues is that sometimes, it takes a different person to look at what we are saying to see it for what it is when we cannot. To me, apart from feeling a bit taken aback by the tone of the newsletter, the impostor syndrome and introversion were the key takeaways - however unpleasant those other thoughts were, I was aware that behind them stood something other than malice, which changes, for me, whether I want to continue to interact with someone, be it personally or via newsletters.

Then, I thought about my own experiences, and people who genuinely reached out to me.

There is a difference between being reached out to and being pushed to work for free. And, as Uncle Ben told Spidey, with great power comes great responsibility. In the world of success making, of being good at something, this power isn't merely using one's knowledge for good, whatever that translates to in your work, but also by paying it forward, by being open to those who are still on the way when we have made it already, or when we are, or seem to be, a step ahead. It's about knowing how not to be elitist, how not to give into the feelings of insecurity we all probably have to some extent, to whatever personal tragedy made us feel we as ourselves are worthless, and that others see that too, and are only around us to use us. It's about knowing that answering a question or sharing what we know doesn't cost anything but kindness, and the time it takes to answer that question.

In my life, and in my career thus far, I have always taken time to respond to those who reached out to me. And I have rarely regretted it. I have mentored, I have bridged gaps between cultural expectations, I have encouraged. Only very few people on this journey turned out to be less than stellar examples of humanity - and this doesn't reflect on me, but on their own insecurities. Nor did I feel, at any point, that they were overstepping...that there has to be a complex process of interactions that go on for months (really, the description of this process reminded me of online scams rather than nurturing a relationship), an unspoken agreement (which is apparently well-known across cultures - trust me, it's not!), some insane adoration of an acolyte for a guru. This does not feel healthy, and no less "exploitative", if we are going to use that word. And let's get real here - the only person who loves you for you is likely your significant other, and possibly your closest loved ones. Professional contacts? We make them to advance our careers, and that's ok, as long as we do not do this in a harmful way - it is immensely rewarding, for instance, to see someone you helped succeed, and being known as a helper of this kind has its advantage wherever people value helping. Where they don't, not so much...but if you can choose, you have a choice - you can choose to walk away from people who do not value you for helping others. Friendship can definitely come from professional contacts, and I think it's healthy; but predominantly, it will start by being interested in the person's work first, and how it relates to our own; and then, when we get to know them better, we might actually really click as people too.

The problem with those who succeed while carrying around the heavy weight of self-doubt and impostor syndrome is that it can very quickly start to seem that they have no other worth to anyone but their success. And especially for those who live off, in part, reaching out to others to draw them in for classes and projects, who actively teach to connect and be interactive and ask for advice, this can be a real problem. On one hand, you are teaching people to reach out - on the other, you cringe every time they do, feeling devalued and probably on some level annoyed and hurt.

Was this what happened to the writer's contact? Maybe; maybe not. We'd have to have both parties tell the story, which isn't possible, to be able to decide. But there is no denying the presence and impact of impostor syndrome in that newsletter.

I have nothing but sympathy for the writer...and, to a certain extent, if they weren't projecting, towards their contact. Will what I read change my approach? Unless I have to contact this person specifically, no. Whatever my impostor syndrome does to me, and trust me, I have one, it will never convince me that I am being beleaguered by people who just want my advice and don't care about me otherwise. I cannot control the ones who do, nor does it diminish me in any way if I still treat them kindly. I will not ruminate about who contacts and why, and wonder if they are just using me, or sitting there laughing at me for being kind. That's their problem, not mine. Kindness and helpfulness aren't negative responses, and those who feel that they are have suffered from broken trust too often, or have internalised toxic messages that see power as a tool never to be shared rather than a responsibility that, like a raft on rough water, means something only when we pull others onto it. This applies to what we can expect from others and to what we can offer. And, of course... If we ourselves have received advice at any point, or wish we had, then we have a duty to continue to pay it forward. If we experience emotional difficulties around the topic, we need to address it, not let it engulf us. If we meet with people who have been engulfed, we can wish them good luck and try to show, through example, that they are wrong about worth and help as they see them.