Mentor's Desk: practical notes on careers, business, ambition and figuring out what comes next

I've been meaning to put something like this together for a while. Most mentoring happens fairly quietly. Someone emails because they are stuck on an application. Someone else has a business idea and is not sure whether to spend money on it yet. Another person has had an encouraging conversation and wants to know whether it actually means anything.
I see the same patterns professionally too, far too often in fact. People talk themselves out of things before anybody else has had the chance to say no. They assume they need another qualification because they do not tick every box. At the other end of the scale, people can become so attached to an idea that enthusiasm starts standing in for evidence.
Sometimes there really is a gap. Sometimes somebody is simply making themselves smaller than the evidence warrants. Sometimes the right answer is to push on, and sometimes it is to stop and check the thing that looks obvious. Working out which is which is usually the useful bit.
That is what I want Mentor's Desk to be. Not motivational slogans, and not me pretending I have always got everything right. I want to share some of what is actually happening in the mentoring work, the good news people send back, the things I keep seeing, and occasionally the lessons I learned the expensive or embarrassing way myself.
Some recent wins
A few messages have landed in my inbox recently that made me smile. I am keeping everybody anonymous, but these are their words.
“Thank you so much! You helped me get my dream job!”
There is not much I can improve on there. “Dream job” was their description, not mine. The work behind it was theirs too. My part was helping them think through the route, prepare properly and keep going when there was no guarantee of the outcome.
“This is incredible feedback, and you nailed my problem.”
That came from somebody building a business after I had challenged quite a lot of what they thought the business needed to be. I would much rather somebody tell me I have found the real problem than tell me I have been encouraging. Sometimes mentoring means saying, “I don't think that is the problem at all.”
“Your advice is incredibly helpful and opening up other routes I hadn't considered.”
This one came from somebody looking at their next career move. We had started with one possible direction and ended up opening several others. That is one of my favourite outcomes, because sometimes the answer is not to become better at chasing the route you already know. It is to notice the other doors sitting beside it.
“You've not only helped me with my CV but my whole perspective on things ... has changed.”
That message stayed with me. We had started with a CV and job applications. Somewhere along the way, the bigger shift was learning to separate “I have a gap here” from “I am not good enough.” Those are not the same thing.
The quieter wins count too
There are others that do not come with a neat quote. A founder has had a positive investor conversation but is sensibly keeping the brakes on while an employment and intellectual-property issue is sorted. Another is doing the unglamorous work of finding actual evidence before building an automation product. A healthcare professional is speaking directly to doctors about what would make them comfortable referring patients instead of assuming price is the only barrier.
There have also been people who have decided not to spend money yet, not to add another qualification simply because they feel stuck, not to trust an opportunity they could not properly verify, and not to make a claim before the evidence exists. I count those as wins as well.
Six months before March is October, right?
Right??? (cue meme)
No. It is not. This is one of those professional mistakes that I can laugh about now, but I certainly was not laughing at the time.
I was in my mid-twenties and still relatively early in handling my own files. I was dealing with a lease containing a break clause. Notice had to be served six months before a date in March. The client was still considering whether to renew and did not want to give notice until the very last moment, so we worked right up to what I believed was the deadline.
In my head, six months before March was October. Then somebody counted it properly: September to October is month one, October to November is month two, and so on. I had served the notice a month late. If the break failed, the cost to the client over the remaining term was around £1.5 million. My stomach dropped. I am fairly sure I went and threw up. Naturally, this all came to light on a Friday.
My immediate manager left me hanging all weekend. I will spare you what I thought of her at the time. I spent those two days convinced I had created a £1.5 million problem and imagining every possible version of how Monday was going to go. On Monday, the managing partner told me he had already dealt with it. Fortunately, the other side had accepted the notice too. It appeared they had made exactly the same counting mistake. In the end, both sides effectively accepted that we had both got it wrong and the issue was resolved.
I am not going to wrap that up in a cheerful “failure is how we grow” bow. It was a genuine mistake and I got lucky, but it permanently changed the way I work. Anything involving dates gets checked, checked again, and usually checked a third or fourth time. Even now. Even when it looks completely obvious.
It taught me something about management too. If somebody junior already understands that they have made a serious mistake, leaving them frightened for an entire weekend does not make them more accountable. By the time my stomach had dropped and I had thrown up, I understood the seriousness perfectly well. Both lessons stuck.
Mentoring is free and subject to capacity. If you think it might be useful for you, or for somebody you know, email mentor@aubreyinternational.com. You can also read more about how the mentoring works and where its boundaries sit.
