top of page

10 things about business life I wished I'd learned sooner

I've been called both wise and a pioneer in the space of 24 hours. I think that translates as old and been around the block a few times, and not necessarily in the right direction. While unsettling, it is also true - and so I am writing away in order to figure out how I got here.

Some mistakes just have to be lived to be learned. They were probably clearly pointed out even as I was making them, yet the connectors between my ears and my brain were just too unformed to hear or process what was being said. Only later, with the pain of experience, was the lesson learned.

But other mistakes were down to gaps and blind spots in the fabric of my context - the background of my thinking formed by upbringing, gender, class, health, generation, cultural background, lack of exposure to visible role models. All that external/internal stuff passively influences our thinking. Eliminating some of these contextual blind spots sooner would have better prepared me to recognise some of the challenges I was facing, so I could handle them with deliberation, not purely re-actively. Improved pattern recognition, as it were.

Before I disappear any further down a philosophical rabbit hole (it must be the age thing) here's 10 business/startup/life lessons I wish I had learned sooner:

1. If you're a "yes and" person, learn the power of a strategic "no" Default "yes and" people have more ideas, more adventures and almost certainly get into more trouble. I imagine they live shorter but more interesting lives than people who greet every situation with a disapproving "no, but". However, your default yes approach will become an overwhelming weakness if it becomes all you can do. For a "yes and" person, no is the most powerful thing you can say - that includes to yourself. No is your emergency brake. You'll need to use it occasionally - you know, like when you're about to hurtle optimistically over a cliff - so it's really worth trying it out from time to time to check it still works.

"No, but" people, ignore what I just said about falling over cliffs - that hardly ever happens. You'll be fine. Try saying "yes and" to everything for a whole day - I've no idea where it will take you, but it will be interesting!

2. The trick is to keep breathing I sometimes think people assume I'm joking when I say my life goal is "Don't die (yet)" The (yet) spontaneously appeared when I hit 40. But under most (not all) circumstances, survival is what we are primed for. So much so that under extreme circumstances the brain goes into danger mode. When fight or flight are no longer the best response options, the human's brain is primed to freeze to minimise further damage, so the person can live to fight another day. That is an extraordinarily powerful thing, albeit one that can lead to psychological problems down the line. But with the exception of scenarios that our brain interprets as so dangerous that it completely overrules our body, every other decision we make involves at least a degree of input from gut, heart and head.

The best way to survive to fight another day is to get to a win/win situation or to delay, reframe or avoid the battle so that you are unlikely to lose. In order to maximise the chances of getting to win/win, I think it really helps to know a full repertoire of battle tactics. Not only so you can play an absolute blinder when required, but also because no one will take your pursuit of win/win seriously if they do not also believe you will implement a win/lose or lose/lose strategy if required. The obvious tactics are always put in binary terms - attack/defence, fight/flight, diplomacy/provocation but it is never that simple. If you are the little guy, you have the most to gain by changing the parameters and the least to gain from dying. Trust me, as well as reading the Art of War and every book ever written on Hannibal, I spent at least a decade playing Pharaoh, Age of Empires and Command and Conquer. That pretty much makes me a General.

3. You don't get better at a game by spending all your time focused on the rules

Some rules - I'm thinking tax and well, tax - have to be followed to the letter in order to stay out of jail. (See above point on survival). But other rules, they just appeared because at some historical point the incumbents wanted to keep other people out of the game, or more nobly, they wanted to stop one side from inflicting hurt or getting hurt. Rules are a set of compromises so we can all kind-of play together with semi-predictable outcomes. But unless you are the referee, the regulator or a lawyer, you can't focus too much on the rules. As an entrepreneur, the way you will really succeed is to get lots and lots of practice playing the game, quite probably learning, testing, bending and adapting the rules as you go.

You won't succeed as an entrepreneur by being better than everyone else at following the rules (though you may succeed in finding the loopholes, although these don't tend to stay open long). I am not advocating unethical or illegal behaviour - very far from it. What I am saying is that you need to crank up your hours of actually doing in order to find your own path and your personal way through the gaps of opportunity. Focusing on following every rule to the letter will not only bog you down, but means you will inevitably go down exactly the same path that everyone else has followed before - fresh opportunity is likely to be very sparse.

4. The pitch isn't level

This means the established home team (whatever that means in your professional world) with their legacy knowledge and legacy network will always have the advantage. You can only seize the advantage by doing something they really didn't see coming. But however brilliant or bonkers your surprising thing - I'm thinking Hannibal taking his elephants over the alps and scaring the Romans - for it to actually work, it needs to land. It needs tactical luck and/or brilliance + visibility and amplification. You may come up with the tactics entirely through your own efforts, but visibility and amplification require the buy-in of others, someone else has to spread the word. This is the critical network to identify, access and befriend in advance. Because you can be sure that if it is left to the home team and their legacy network to spread the word, the news story will not be about their humiliation, but yours.

5. Hard work on its own doesn't get you what you deserve

If we were in an ideal, closed-loop system of work we would work very hard, be great at our job and our outputted efforts would become a direct input to our success. Many of the women, introverts and fairness-seekers I know have laboured hard and brilliantly for years either believing or wishing they were in such a system. They are frustrated, hurt and demotivated when their hard work isn't recognised and rewarded.

That isn't how the system actually works in business. I am sure there is some sensible, famous theory for this, but I don't know it, so I have made up my own. There are 3 components:

A: The doer Our hardworking brilliant hero - let's say you.

B: The beholder Your boss, board, investors, parents, etc. The person who can bestow rewards and recognition on you, our heroic doer.

C: Interference in the system Some of this is benevolent interference. Due to harmonics, fairy-godmothers or some marvellous sound/media property, this interference picks of the signal of the doer and clearly amplifies it to the beholder and beyond. This is good interference. Then there is neutral interference - background noise, stuff happening, general distractions, time pressure on our beholder. The intent is neither good, nor bad, but the outcome is that some or all of the doer's signal is lost and the beholder never fully picks it up. Therefore the outcome is bad for our hero. Finally, there is malignant interference - one of the things I hate most in the world. This is where some useless, ignorant, nasty, lazy or plain malevolent so-and-so takes credit for the doers signal and claims it as their own. They may even go further, making effort to sabotage, discredit or neutralise the doers signal. Unchecked, this is catastrophic for both our hero, the beholder and the beholder's business.

All three types of interference exist in every system and we owe it to our own effectiveness as employees, founders or leaders to understand that. The best leaders are aware enough of the risks of neutral and malignant interference to develop processes to hear what every doer has to say - but most don't do this effectively enough. This is an incredibly difficult problem to tackle solely from the bottom up - though that doesn't mean it shouldn't be called out. But from now on, this will be on my radar from day one - and malignant interference will never be tolerated.

What can you do as an employee - especially if you are the one getting talked over, having their ideas stolen or in one of the toxic "team" situations where it's their way or the highway?

Work on removing as much malignant and neutral interference from your personal signal as possible and seek direct channels of communication where possible. One of my employees was exceptionally good at this - she'd make sure our 15-minute one to ones always took place, even if they needed to be moved around multiple times to work for me. Without running over time, she'd always tell me why she (and her team) was great, what they were up to, why I should care (as in business impacts/risks) and exactly what she needed from me next. Did I ever resent her asking? Not at all - she didn't always get it, but I respected the efficient, clear communication and the absence of too much confusing or contradictory interference that would require picking apart and analysis. Her approach meant I could make better, faster decisions - and kept her front of mind.

6. Don't let your energy, sanity or business be destroyed by toxic manipulators

Since opening up the conversation about the devastating impact psychopaths and extreme narcissists can have in the startup, I have been interested in just how many of you have been in touch to share - and sanity check - your own workplace stories. Too many of these involve background misogyny and general rotten behaviour. But some of the most extreme stories clearly suggest toxic manipulators at play, so much so that during a recent fundraising webinar, we had a frank and useful discussion on what founders can look out for. Here's what we came up with.

To start with, it helps to understand whether you are dealing with a narcissist or psychopath (if it's both at the same time, stop reading now and run). A psychopath is preoccupied with winning, while a narcissist is preoccupied with being appreciated and admired. A narcissist will rewrite history to make themselves at the centre of the founding story, whereas the psychopath will play the long game and simply take the company and/or its resources. A psychopath manipulates to do as little work as possible for the purpose of having money without expending effort, and may even pass off the bulk of their job to juniors. A narcissist may demean and insult you, mess with your reputation, and throw you under the bus if they perceive you as a threat, but doesn’t mind working hard if it leads to approval and boosts their sense of superiority.

These people will beat you by emotional and financial exhaustion if you play them at their own game. They have a lifetime of practice and are wholly focused on sustaining that game, whereas your priorities are (or at least were until they got inside your head) focused on building your business. In a leadership position, their burden on the business is so high, that if you don't recognise and deal with it immediately, it becomes virtually impossible later.

But what if it is too late and if avoidance really isn't an option? New tactics are required. Don't ever compromise your values, but learn to quickly recognise the signs that you are in the company of a manipulator who will use those values against you.

Document everything. At best try to engineer a win/win situation that looks like a 'you lost and they won' scenario. (They will gain no satisfaction from a win/win, they need to feel they beat you before they'll willingly move on). Depressingly enough, that may include buying them out or you walking away. If you are prepared to make a show of force, be ready to follow through on that show of force, even if it takes you into irreversible lose/lose territory. As one founder told me, in the end blowing up the whole company and starting again was the only real option left.

Highly manipulative psychopaths and narcissists don’t respond to empathy or compassion, in fact, they may despise you for the implicit weakness in that. Instead, they respond to actions and consequences, and so must you. Some of the behaviours to watch out for, and ideally catch them red-handed at, are:

  • Blatant lies

  • Policy violation, especially around treatment of junior staff

  • Financial, ethical or governance breaches, omissions and fraud

Unfortunately, gaslighting (implying you're mad), deniability (I never said that, or surprise u-turns in viewpoint), and blatant blame shifting are not strong enough angles - though building an evidence base will at least reassure you that you're not imagining it.

Ideally, you'd never let them in to start with - but they are so charming and interview extremely well. Reference check every hire and go overboard with executive checks - including the little details like proof of exams and professional awards. Manipulators love to exaggerate about this stuff, and little lies and inconsistencies are often where you'll catch them early.

But if it comes to it, fight early, fight hard, and be prepared to feign or allow yourself a 'you lose/they win' result. That way you survive to thrive another day. There are a nice people out there - go have therapeutic coffee with lots of them and restore your faith in humanity.

7. Don't worry about tomorrow's problems at the expense of today's

I used to use my 4am, 3am fears as a way to prioritise what to worry about the most. As in the more terrified I was at 3am or 4am, then the higher priority the problem. But I think at least 50% of what I was worried about at any one time were tomorrow's problems - problems several steps away, or several chess-moves away if you like. I was trying so hard to balance looking forward and day to day execution, that I gave future problems too much headspace. The problem with these problems is if you fix them first, you are over-optimising for a future scenario that may not play out or may be drastically changed by the way you solve the problems of the here and now. They should absolutely be on your radar, but it is inefficient if they occupy too much of your day to day attention, if you are primarily in execution mode.

There is a better way, and we actually nailed it to some degree as a board of directors of the Digital Analytics Association. We would have facilitated board retreats where we focused only on future problems and strategy and did so completely separate from any day to day operational challenges. We devoted time to quality strategic thinking, rather than trying to balance it in the same headspace as operational thinking and firefighting. Perhaps it's just a limitation on the part of my mind, but the last few months of being able to better timebox my thinking between operational and strategic has really highlighted to me how hard it is to actually do both things simultaneously and well for prolonged periods.

8. Unleash your power (but don't let go of it)

Power's great. I'll have some more of that, please. I appreciate that probably makes me very unladylike in some people's eyes - but seriously, what is not to like? Power is the ability to make decisions and choices that affect yourself and others. Power doesn't have to be about running companies - power in its basic form is self-determinism and self-responsibility. The commitment not to leave your fate entirely in the hands of others, but to take the steps - and accept the risk - of making your own choices. I would, until recently, have said it was impossible for power and responsibility to be completely independent of each other, then along came Trump.

Where there is great power there is great responsibility, where there is less power there is less responsibility, and where there is no power there can, I think, be no responsibility. Winston Churchill

No one should be ashamed of seeking or using their own power - we should celebrate that. The interesting thing is, in my experience, we generally don't. People can be surprisingly uncomfortable about those who are comfortable with their power and their ability to lead, especially when that person is younger. So the subtle pressure to give that power up, to share it, relinquish control, generally be a bit weaker and more compliant begins. I actually didn't see it for what it was as it played out around me, so my comfort in my own skin led me to make a mistake that would give Shakespeare a wry smile. I voluntarily and unnecessarily gave up some of my power for noble (and probably highly egotistical) reasons, and that decision came back to haunt me.

Be very careful who - if anyone - you give your power to. One for the English Literature graduates - if my last company was a Shakespeare play what would it be? Hmmm, let's forgo the obvious Scottish play and select Othello, what with Iago the psychopath, Othello the insecure, status-conscious general and Desdemona, the innocent but now absent-on-account-of-being-dead heroine. Which character am I? Oh, I am dumb-ass King Lear, off in a completely different tragedy, busy voluntarily giving up my power to Regan and Goneril and then being all surprised when it doesn't end so well. (For the non-Shakespeare fans, that is a bit of an understatement).

There is a difference between power and control - by retaining one, you can still choose to relinquish and delegate the other, but you will do so from a place of strength.

9. If you're happy and it's working, then so what?

One of the things I regret is that I didn't take more time to celebrate and enjoy my first little lifestyle business, which made me and my partner very happy. It was hard work, but fun. It was never going to scale or have an exit, we never raised a penny of investment (though it was always profitable) yet by only measuring it to other people's standards, at the time I didn't think it was a success at all. But we went to amazing places, did interesting work, had nice clients - and we enjoyed it. By the end, I was ready to move on, learn more, do more, go faster, but that doesn't take away from the fact that business was a really decent achievement and a success, I was simply measuring it on the wrong scale.

In startup land, there are so many people telling you how it should be done (even though most of them have never done it themselves). And if you are entering awards and raising money like most startups emerging from incubators and accelerators have been trained to do, there are so many people measuring you based on arbitrary yet standardised measures that entrepreneuring can feel a bit like being paraded in a cattle market or a pony show. I have found myself advising other founders to understand what cookie cutter they fit into and focus on getting traction accordingly.

But what if you don't fit a cookie cutter and you're happy anyway? You are enjoying your journey for the journey? Congratulations - maybe you just found the meaning of life.

10. Go for what you want. You won't please everybody anyway

I find it peculiar that "people-pleaser" has been turned into such an insult - a negative characteristic that should be surgically extracted from anyone (or should that be any woman?) who wants to be taken seriously as a leader. As far as I am concerned, any neurotypical person who is not a total jerk is in at least some way a people-pleaser, and the world is a better and more civilised place because of it.

But I do see people unwilling, unable or simply unprepared to ask for what they want for fear of how they will be judged by others, or in case their wants may somehow negatively impact others. So they wait for the day they will be noticed, and meanwhile, put up with an inferior option. And most frustratingly, sometimes those "others" who were given such consideration, never display it back, while leadership fails to recognise what is going on. It is impossible and unnecessary to please everyone - but seek out those who are interested in what you want to achieve and can help you make it happen. It is not a zero-sum game (unless you are a character from point 6) - your success and progress do not have to come at the cost of someone else's, especially not when you are making your own path. Ask for what you want - you may not get it, but what you will almost certainly get is a map. Then you are on your way.

Those of us who have got old enough to be comfortable in announcing our own triumphs must look around and see who else will benefit from having a little light shined on them. Ask them what they want, ask them how you can help and enable some else to take their first steps on their own path. I reckon that for every hand that has ever pulled you up, you should be able to pull five or six additional people up too. That's not weakness or people-pleasing - that is simply being a decent human being.

Historic Posts
RSS Feed
  • YouTube - Black Circle
  • LinkedIn - Black Circle
  • Twitter - Black Circle
bottom of page