16 rules to get from the bottom to the top

Matt Casey

Written by Matt Casey. Co-founder of DoThings. Author of The Management Delusion and We Need to Talk About Scrum.

February 27, 2020

Success did not come easily to me. I had what could politely be called an unconventional childhood. By the age of 14 I’d dropped out of school to work a less than minimum wage cash in hand job, and I was living in a room I could not afford in a shared house I should not have been living in. Looking back on it, it’s near enough a miracle I was able to keep myself alive. My career prospects did not look great.

I’m 40 now, and my life is objectively pretty great. I made it. But I came up hard. There were so many awful jobs, so many disappointments, so many people who seemed determined to make it difficult for me, and above all, so many of my own stupid mistakes.

The following is a list of some of the most important things I learned as I went from being a feral kid who could only afford to eat every other day, to being able to live my life entirely on my own terms with no financial pressure at all.

Don’t mind that it hurts

Intelligence and talent are helpful, but to be honest nowhere near as helpful as you might think. I don’t have that much of the former, or any of the latter. It actually doesn’t matter that much. Insecurity about our ability holds us back far more often than a lack of ability does. For a long time I felt inadequate and incapable of becoming more than I was. I didn’t feel like I could change my life, and I was so scared of failing, I didn’t even try. What I wish I’d known was that it would never get easier. That there would never be a moment where it wouldn’t be scary to try. I just had to do it anyway.

There’s a scene in Lawrence of Arabia where Lawrence slowly puts a burning match out with his fingers, without showing any signs of pain at all. William Potter then tries the trick himself, and yelps in pain.

“It damn well hurts! What’s the trick then!?”

“The trick, William Potter”, Lawrence says, “is not minding that it hurts”.

If you feel like you’re not good enough, that’s probably not going to go away on it’s own. There’s no trick to feel better about that. The trick is to just not mind that you feel that way and try anyway. I’ve felt inadequate my whole life, and no amount of success I’ve gained has changed that. I just don’t mind anymore.

Do something… anything

For a long time I didn’t know what I wanted to do. I didn’t know what career to pursue, and nothing felt like it was for me. So I drifted and did nothing. Then eventually, I just picked something. It happened to be tech. I didn’t know it was the right choice for me, I just knew it wasn’t nothing. My goal was to be a software developer. While I was trying to do that I learned enough about computers that I could get an IT support job, and that led to a management position, and that led to the career I have now. Doing something put me in a situation where I could find the thing I should be doing. It didn’t matter that the thing I initially picked wasn’t right.

If you want your life to be different, you have to do different things. If you can’t think of a guaranteed way to improve it, just do something anyway. If you’ve rolled a 3, and you never roll the dice again because you’re worried you might roll a 2, you’ll be stuck on 3 forever. But you can roll the dice as many times as you like. If you roll a 2, roll again. If you roll a 1, roll again. Keep rolling until you get a 6. You don’t get any guarantees when you make a change, but you don’t need them. You just need to keep moving.

Do more than your job

No matter what your job is, try to do more. There are always ways you can help and you should make yourself available to your manager for anything and everything. The more you do, the more chance you have of being noticed and given a new opportunity. If you ever say, “that’s not my job”, you’re making a huge mistake. Everything is your job. Every bit of career progression I have ever achieved started with me doing something that wasn’t my job, and me taking it on enthusiastically.

When you go to work, always look for ways you can do more. People will notice.

Don’t moan, but do give feedback

The way you know the difference between the two is simple. Ask yourself why you’re saying the thing you’re saying. If it’s to get something more for yourself, then it’s moaning. If it’s to make the company or the team better, it’s feedback. Always tell your manager if you can see a way things can be better - just by raising it you give yourself a chance to be involved in fixing the problem. But if you’re constantly asking for things for yourself, don’t expect to be top of the queue when opportunities come around.

The first management break I got was in a department that I was constantly complaining about. At the time even I thought I was moaning, but looking back I realise that the reason the owner decided to put me in charge was that nothing I was complaining about was personal to me. I wasn’t saying I wanted more, I wasn’t complaining about what was happening to me. I was complaining that as a team we could and should have been doing much better than we were. It did ruffle a lot of feathers, but if I hadn’t said it he would never have noticed me, and never even considered that I might be the answer to his problem.

Do your job as well as you can do it

This sounds obvious, but far too many people decide that they’re too good for the job they’re doing, so they don’t take it seriously. The result is they’re never trusted to do anything more. Always do the job you have as well as you can possibly do it, no matter how far beneath you you think it is. Otherwise you’ll never get out of it. It’s very difficult for a manager to promote you to a role they want you in if you haven’t been taking your current one seriously. It would cause problems with the rest of their team that they won’t want to deal with. Make it easy for your manager to promote you by being great at the job you have now.

Never Sulk

This is a mistake that I’ve seen people make so many times and it’s one of the most depressing to see. Sometimes you’re going to miss out on an opportunity you deserve. Someone else will be slightly more suited to it, or things just won’t come together at the right time. When this happens, you’re going to feel down about it. That’s ok. Go home, shake it off, then come back to work and go after the next opportunity. If you sulk, you lose. Nobody else does.

I understand the urge to sulk, I really do. If they don’t appreciate you, what’s the point, right? But failing is part of trying. If you’re going to go for opportunities, you’re going to get overlooked for a lot of them. Most of them in fact. When I got my promotion to Director level, I had already been overlooked for the promotion three times, each time for someone who I didn’t believe was as deserving as I was. If I’d sulked, if I’d had a tantrum, my boss wouldn’t have suffered one bit. I wouldn’t have been “showing him”. I’d have suffered, nobody else. So I didn’t. I tried to see it from his point of view, I recognised there were some skills those people offered that I didn’t and that he simply valued those skills higher than the ones I had, and I carried on trying. Eventually, I got the job I wanted.

You don’t know how many times you’re going to be unlucky. What you do know is that giving up guarantees failure, so you might as well keep trying. Some of you will be unlucky and miss out 10 times as much as someone else. But keep going anyway.

Remember your boss is human

More than anything else on this list, this is the thing I wish I’d understood when I was younger. Your boss is fallible, because they’re human. Don’t punish them for making mistakes. No matter how great your boss is, they will make lots of them. If you’re the kind of person who gives them grief for that, they will quickly stop engaging with you. It’s a really hard job, and they want a supportive team who help them, they don’t want to feel like they’re in trouble all the time. Your boss will promise things they don’t end up delivering, your boss will be insensitive sometimes, your boss will be unfair sometimes. Get over it, they’re almost certainly not doing it deliberately. Cut them some slack, and try to help them as much as you can. In return, your boss should be supportive and understanding when you make mistakes. That’s the relationship that you want to have.

Don’t say you deserve a pay rise, ask how you can earn a pay rise.

I wish to god it hadn’t taken me so long to learn this. Asking for more money for doing a good job doesn’t work - they expect you to do a good job. In fact asking for more money at all doesn’t work. Never ask for more money now – ask how you can earn more money in the future.

Don’t say, “I’d like a £10k raise today”, say, “I’d like to earn £10k more in 12 months time, can you help me achieve that”. As I explain in detail in another post, this is pretty much a pay rise cheat code.

Always ask for the top of the range.

Salary isn’t fair. Stop thinking it is. Your salary has almost no connection at all to what you deserve, so get that out of your head.

When you’re offered a job, that is almost the only point you’ll have any real power in salary negotiation. If you’re being offered the job, a lot of work has gone into finding you. No right minded manager would pick a worse candidate just because they were asking for slightly less money than you, so when you’re asked about salary requirements, ALWAYS ask for the top of the range. No matter what you were paid before. If you’re currently on 50k, and the salary range for the new job is 60-70k, ask for 70k. They want you, that range has been approved, and they’ll probably give it to you. The worst they can do is say no and give you a counter offer. They almost certainly won’t just withdraw the offer, and if they do that, that is not the kind of company you want to work for, so you dodged a bullet.

If you don’t know the range, ask the recruiter. Recruiters tend to work on pecentage fees, so it’s in their interest that you’re paid more.

Don’t let fear of change limit you

If you’re in a job and you’re not getting what you want out of it, leave. If you have to take a pay cut in the short term, do it. If it won’t be as much fun in the short term, do it. Don’t take the easy path that leads nowhere, take the hard path that leads somewhere.

Be open about what you want

If you don’t tell people what you want, how can they help you? People often worry that if they tell their manager that they want something more than their current job, they’ll get angry. Even if this is true, consider this: if there are two types of manager - the ones that want to help you succeed, and the ones that don’t care - do you really want to work for the second kind? If you tell you manager what you want to achieve and they get annoyed with you, then you don’t want to work for that person and you should get out immediately. They will only hold you back. You can’t annoy a good manager by telling them your ambitions.

Work hard, leave the games to the others

Some people play games and get involved in work politics in order to get what they want. It can be moderately successful, but it never works to any significant degree. There are lots of reasons for this. Firstly, if you think sucking up to your boss or criticising other people who you’re competing with for roles is working, it probably isn’t. Good managers will know when you’re doing it, and they will use it to their advantage, not yours. Bad managers might not notice you doing it and you might get somewhere with them, but they’re terrible people to attach yourselves to because they won’t ever achieve anything great themselves. Why have a failure as an ally?

If you play games, you’ll either get away with it with someone useless to your future, or you’ll alienate someone who could have been useful. Just be the best you can be every day, help the people around you as much as you can, try to make the place you work better for having you there, and leave the silly game playing to other people.

Learn useless stuff

I have learned so many skills I don’t need. I’ve tried my hand at graphic design (horrible results), software development (my CTO threatened to murder me), Copy Writing, UX Design, Type Setting books, advanced Excel tricks, personal training, and god knows how many other things. I suck at most of them, but one of the things I learned about that I didn’t include in that list is people management. I gave that a try, and that’s what finally gave me a career. When we wait for a reason to learn something, we often never find that reason. So just learn pointless stuff, the reason to know it might come around later on, and when it does you’ll be ready to take advantage.

We are lucky enough to live in a time where as long as you have an internet connection, there is literally no skill you can’t start developing with no cost other than your time and effort. So learn something, anything. You never know where it will lead.

If learning is part of your routine, one day you’ll realise you suddenly add value that you didn’t add before. I spend part of every day actively learning something. I always have a book about something related to work on my kindle, I subscribe to podcasts about random things that might teach me anything, and the moment I meet someone who is good at something I try to learn from them. I ask them questions, I watch them, I think about why they do the things they do. You can always be learning, but you have to engage with the process. Don’t be shy about asking for help, people tend to actually want to give it to you. You can never stop getting better, and the better you get, the more valuable you are to a company.

One thing I wish I’d known when I was a younger man is the value of being given knowledge. Early in my career I happened to have a job where they gave me extensive Management Training. At the time I didn’t think of it as anything particularly significant, but it shaped my entire future. At that time I remember complaining to my boss that I was underpaid, and feeling like I might quit because I wasn’t being rewarded fairly. I often shudder at the thought that I could so easily have quit over a few grand a year and missed out on this genuinely life changing opportunity.

Always consider the value of what you’re learning when thinking about your reward package. In the early stage of your career, what you learn is far more valuable than what you get paid. Getting paid 20k and learning from someone who could really teach you something is far more valuable than getting paid 30k and not learning from anyone. Collect as much skill and knowledge as you can, it will pay off.

Look after your neighbourhood

Don’t ever treat anyone at work as a competitor, even if they might be going for the same promotions as you are. Do the right thing to get the result for the company, and don’t ever think about how you look compared to anyone else. Trust that the right people will notice if you do good work. One of the best managers I’ve ever had picked me for a promotion once over a lot of other guys who were more qualified and experienced than I was. When I asked him why he picked me, he said “I always notice if good things happen in someone’s neighbourhood”. What he meant was that he notices if someone is always around when success happens, whether he can directly see what they did to contribute to that success or not. He knew that it almost certainly isn’t a co-indence when that happens. The most successful people are experts in spotting the people who make a difference, so don’t feel like you need to shove it in their face. They’ll find you, just try to make good things happen in your neighbourhood.

Don’t get dragged down by others

I have seen far too many occasions where one negative person ruined the career chances of several people they worked with. If you work with someone who doesn’t care enough about their future to take their job seriously, and you associate with that person and get dragged into their behaviours, you’re selling yourself short. Work friendships are essential, but they have to be the right ones. Of course you have to enjoy being at work, and having a great friendship group is crucial to that. But be careful who those friends are, and make the hard choice of ending friendships with people that get in the way of your career. You should value and honour the relationships you build at work, but if someone doesn’t show you enough respect to understand that you want to be successful even if they don’t, they aren’t people you should have a relationship with.

Get your head right

When you’re at work, only ever think:

“How can I help my team”

“How can I help my manager”

“How can I help the company”

That isn’t just something you say to yourself, you need to train yourself to genuinely feel this way. The moment you do, success will follow. If you think, “how can I help me”, people will recognise that in you, and you won’t progress the way you want.

If you try to look after yourself, nobody will bother looking after you. You know who can give you a pay rise? Your manager. You know who can give you a promotion? Your manager. Long story short – you need your manager to support you if you want to get what you want. If you just concentrate on looking after yourself, your manager won’t look after you. Look after your manager, and it’s in their interest to do the same for you.

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