Things I wish I'd known earlier in my career

Expanding on Vitaly Friedman's post on Smashing Magazine, I'm looking back at what I myself wish I'd known earlier in my career.

Table of Contents:

I saw this post from Vitaly Friedman on and it resonated well with lots of realisations I've had recently about my own career. So I wanted to compile my own list of things I really would have wanted to know earlier.

It is important to me to mention, that I don't write this with regret or resentment for me or my career nor to I wish to undo my decisions. At the same time, as a more mature person and experienced tech worker, I would like to share my own insights with other people on similar trajectories, not so that they do it differently, but so that they have another perspective to potentially consider, and ultimately become more empowered and self- and pro-effective.

I've done a lot of waiting and observing, and while it sharpened some skills, it didn't necessarily lead to progress in my career. It did the opposite, it reduced my momentum. And you can do a lot with momentum.

Vitaly elaborated on these points beautifully:

I've come to similar or identical conclusions, in varying degrees. The points I am adding on my own may or may not apply to you in varying degree.

This is more a list to myself, a record of a dialog I've been having with myself, made accessible to whom it may concern.

Separate the craft from the industry

Section titled Separate the craft from the industry

I saw the actual practice of making websites, designing or developing directly intertwined with the larger industry. The ideals of the craft must be the ideals of the industry as well. This led me into many conflicts, in which the needs of the business clearly outweighed the requirements for good craftswomanship.

This classic conflict would not subside in me, until I eventually had to accept both realities, with their value systems and their goals, as existing in parallel. All conflict is resolved by decision. By deciding that the ambivalence between craft and industry are something I am indeed well-equipped to hold, the conflict had turned into possibility.

Rarely do the interest of automated business align with the interest of craft, not just on the web. Craft itself is always concerned with creating the best result possible. The result of our craft is served and offered to people to interact with, meaning that much of its quality is determined by the receiver. Consequentially, craftswomen align their craft around those peoples needs.

Industry on the other hand, does not care about the needs of the people - unless they can directly tie it to monetary gain. That is the point of a business. Industry is the larger application of this intention.

There is great freedom in accepting both as independent value systems, that are not fighting for objective evaluation and rigid hierarchical alignment, instead, they can ambivalently live together, in symmetrical relationship to us.

What I mean by that, is that we allow ourselves to compartmentalise and confine the needs of the industry and the craft respectively to their own contexts. If a client asks us to make the logo bigger, even though we knew it would be a mistake, we may speak up and advice against it, but if we accept this request as an expression of seeing a business need fulfilled, we can approach it respectively and allow ourselves to not see it as a devaluation of us as craftswomen, if we go along with it. Because in this interaction, we are not only paid as craftswomen, but also as employees, contractors or suppliers - or experts of process, not result. And in these contexts, the need of the craft are not primary.

Learn to ask questions, then ask questions

Section titled Learn to ask questions, then ask questions

This is the one thing that I am sure would have improved my movement in this career, had I learned it earlier. Learning to ask questions as a discipline has become integer to me as a systemic counsellor (in training under supervision). In systemics, we accept all reality as constructed, meaning that all external descriptions of reality are merely offers that can be accepted or not. Instead of "educating" my clients about how to think about things, I ask questions that may allow them to construct alternatively themselves.

This same principle can apply to the way we interact with stakeholders and other people in our industry. If instead of assuming to be experts in our fields, and thus experts in what our clients and stakeholders need, we assume to be experts of helping our clients and stakeholders express their needs themselves, we become experts of process. And as experts of process, we become focused with how we do things, not what it will lead to. Because if stakeholders and clients have the ultimate say in what gets accepted or not, then they are the experts after all.

But what we can do, is ask questions - questions, not intended to add information to us, but to them. This is a bit of an art form, but for the sake of this little post, I'd like to give you a few examples of solution-focusing and circular questions, that I have borrowed from my counselling practice and that have proven to be helpful in my design & dev career too:

None of these questions are intended to give the person asking the question information. Instead, they are intended to create new information within the client itself. I've asked these questions to clients directly and if they have a hard time answering, then that is usually a good sign. It means, that before asking that question, they haven't thought of it before. Yet, asking what to leave intact on a website redesign is not only a really valuable information to have for the process, but it also important for the clients to get a better feeling of what they want and need.

Same goes for asking circular questions. Circular questions are asked in order to gain information about relationship dynamics, without having to have all the people in the system present. For our context, there is a system and a dynamic present between our client and their users / customers. We can never gain objective information, instead we ask the client about how they are experiencing this dynamic: "What would your users tell me, if I asked them right now..." - This question invites clients into a meta-position, in which they are observing themselves / their business / their website from a user's perspective. You'd be surprised about how specific and accurate these answers can become, or how shocked they are, if they realise that they actually do not have an accurate enough picture to answer that question. In the latter case, this is what you need to focus on.

This is just a small excerpt about how I am approaching questions nowadays. I believe that as experts of process we need to become masterful questioners.

I would like to focus Why-Questions for a short moment. I picked up the idea of the 5-why's very early on and started using it. It made a lot of sense to me. Nowadays, I avoid "why" as much as possible. The idea of the question is to find out about how someone else sees something, what their logic is, what their reasoning is.

But why as a question can be a spearhead, a weapon that stings. Instead of inviting people to reveal their thoughts, it may force them to justify themselves. And to that, we have no right to ask stakeholders to justify their choices. Not only does it danger the complementary (hierarchical) relationship we are in, it may create a power dynamic with us at the losing end on it.

Instead of asking "why", we can ask "what for" - as in, "what will this be good for / achieve?" - not from a place of disbelieve, but from a place of respect for the desire behind the request, with the intention to understand said desire. Another way of getting to the same place, is to frame it a bit differently, like: "At the moment I don't yet understand what you are improving with this change - can you explain it to me so I can support you better?".

The gist of it is that the question "why" is often an attack - try to avoid it.

Don't stay for the "potential"

Section titled Don't stay for the "potential"

I have spent years in companies, waiting for an either promised or imagined reality, that never came to be. I joined and I saw potential of how good things could be, and I saw myself thriving in this potential reality. And while I poured my heart and twenties into these companies, the potential went unfulfilled until it eventually rotted away and I was forced to start anew.

I did not see this pattern until very recently. Now I know, that staying with a company for how things could be, is a draining and dooming attitude towards yourself. If we allow ourselves to remain in unsatisfying and lacking situations and circumstances, despite having the choice to go another way, we are treating our own needs and also our time with disrespect.

We see all this potential, and we believe that if we just stay for long enough, and if we just fight hard enough and pour enough of ourselves into the company, it must eventually lead to the fulfilment of said potential, with us thriving in it. And it may happen, but if we stay for the potential, we are just gambling with our time. Time, that could instead be poured into a position that is giving us what we need.

I don't regret my time that I spent waiting, suspended and having to understand that things just can't be different right now, but that the company after all is growing - but looking back I can pinpoint exactly the time when a part of me already knew that it would be doomed, and yet I stayed, leaving only me to blame for it in the end.

If we want to achieve certain things in our career, we are left alone with it. Especially as a queer person, even though I am still much less discriminated against, I am still over mentored and under sponsored. The only way forward, is to be self-sufficient and pro-active when it comes to my career choice, because nobody else will lift me where I want to go. I need to go there myself, and so do you.

Always be looking at open positions

Section titled Always be looking at open positions

In order to have movement, you need to be able to have possibilities. Without options, there is no movement. This applies to your career. Always be aware of other potential positions for you to apply to. In our industry, increasing your salary is only really possible by hopping from one company to the other, as Vitaly has already pointed out in his article. I didn't know that. I had to turn 31 to come to this realisation.

If you are like me, you might have grown up in a time, where older generations proudly talked about how long they had been with a firm and you may have sensed a feeling of pride and respect. This is a generational artefact that most of us will never experience. This thinking is so old, that nowadays, if you are not changing companies every 1-2 years, people will assume something was wrong for you staying this long. This has happened to me before, in which I was asked to justify myself for staying with a company for so long, despite not getting into higher positions.

Even if you are not intending to step up the career ladder, keep looking and maybe even applying to other positions, in order to know what the market expects you to be capable of. Your job may not offer you the possibility to learn and master tech that maybe other companies will require you to be experienced in, should you lose your job suddenly.

Be loyal to the people, not the business

Section titled Be loyal to the people, not the business

As is true for separating craft from industry, it is valuable to differentiate business from people. I never separated these two, because I've never worked inside huge corporate environments. So asking for raises, different hours, or saying no to the business automatically meant asking for things or saying no to that person that I was on a first-name basis with. But it is very different to ask for a raise from a friend, or to ask it from a company.

As you build relationships to the people over time, try to separate them from the interest of the business. We can be accepting, loving and tolerant with the people, while at the same time remain firm, confident and in-control with the business.

When we ask for a career plan, the people answering, are representing the business, not themselves. And as we ask, we are not asking as people, we are asking as employees. Same principle applies to interacting with clients, even as freelancers. As people, two individuals working together on a project, being welcoming, understanding and empathic is required to a positive relationship, but as a one-woman business, I may have interests to protect that are directly tied to my existence as a person in this world.

Ultimately, it is practicing separation of concerns. As humans in friendly relationship with each other, we have different concerns than the business who are dancing through a carefully orchestrated transaction.

I believe that we are reaching a point in tech, where we are automating more positions than new positions are opening. It certainly is the goal of tech to make people redundant. And in an ideal world, all of these people would move on to other jobs. But that is not the reality. Some people will move up and move on, but many people won't.

If I were to join tech at this time, I would make sure that I had a backup plan. I believe in diversity and I personally learned that I have to not focus too hard on one thing, but instead learn to balance many things simultaneously.

In a way, this sentiment is also expressed by Vitaly's point of thinking early about passive income. But the truth is that most people working in tech are not present on social media or even have the desire to invest even more time in addition to their already cognitively and socially demanding day job. It certainly is an attitude that we are seeing as a result of generational change and I believe it is rather healthy.

Your job may just be a job and that is fine. But tech is only a secure job if you are willing to switch gears at any given point in time and if you are willing to do the industry's bidding, maybe even forcing to ignore your own morality in the process of it. There is no denying the volatility of even the smallest aspects of tech.

And let's not forget the fact that sitting for hours on end, no matter how much you are stretching in between, will either force you to counter-balance it (inadvertently sacrificing even more time on the job, because you are trying to undo damage) or deal with the consequences later on.

Chances are, that you are working in a company that is held "exit ready" at all times. That means, that they are making sure that if push comes to shove, the few people invested in the company can sell it and exit the business, leaving with a profit in the process. And I think as tech workers we need to do the same. This doesn't mean that we should prepare for a doomsday scenario, but it may be wise to widen our options, consider an alternative or maybe complementary path. Keep your options open and diversify. Companies do it too.

Don't take career advice from anyone

Section titled Don't take career advice from anyone

As a systemic counsellor, I am aware that no reality is constructed from the outside. Via communication, messages are decoded, sent, received and decoded. A famously lossy process in which meaning is given to what was decoded, not found in it. All interventions are offers, invitations of alternative constructions, but the construction is done by the client, not the counsellor.

For that reason, I think it is in general not a bad idea, to think of all career advice with an asterisk that reads: "May not apply to you".

Come to your own conclusions and where as well intentioned people can become powerful allies, mentors, sponsors and friends - but making their interpretation of our career a requirement for us to pivot is not a good idea.

Aim to be as self-sufficient as possible - while at the same time not thinking that all success will always ever only come from you. All success has a component of luck or at the very least privilege playing its part. But I've come to understand that if I want to be autonomous with my career, I need to to be sure that I am able to move on my own. And for that I need options, the ability to discern and a little bit of momentum.

My last piece of advice I would give to myself would be to not take it so seriously. If a feature wouldn't end up how I designed it, if an animation wouldn't turn out how I envisioned or prototyped it or if a stakeholder just needed to take a dump on my work in the very last moment, it would feel like someone had eradicated all my time and effort. My ego was so hurt that it would keep me up at night, forging plans to save myself from yet another loss. Working became a game of counting wins and losses, hoping that eventually, it would turn out in my favour.

Yet at the same time it prevented me from seeing the possibilities that these situations also had offered me - including the compliments about how I had approached my work. If the end result can only be a win or a loss, nuance gets lost and instead of seeing lots of small wins and a few small losses, it turns into one general loss that overshadows everything else, eradicating all the things that went well.

So nowadays I approach most of my work with an explorative mindset, with the knowledge that if things don't turn out well, that other things will have gone very well and if push comes to shove, I'll be able to deal with the situation as it happens, and with its consequences as well.

So that's it. That's what I would tell myself retroactively. I wonder what advice I'll give myself in 10 years, if I still work in this industry that. Though don't mistake, I'll still be writing HTML & CSS, I just don't know if I'll get paid for it! :P