That one thing: a deadline. And it needs one now.
Right now I’m probably sounding a lot like a ‘Seagull Manager’ you might have dealt with in the past. The detached, high-level executive, usually nowhere to be seen, who will storm into a room full of hard-working team members unannounced, raise alarms (off the back of very little knowledge) and provide criticism without much real insight… all before making a dramatic exit in a frantic manner. Or as the pioneer who first observed this phenomenon, Ken Blanchard, more elegantly puts it in his book, The One Minute Manager:
“Seagull managers fly in, make a lot of noise, dump on everyone, and then fly out.”
No – my advice, to you, to place a deadline on your project: comes not from an attempt to meet a senior manager’s angered demand, but rather from a place of having previously crafted creative fulfilment.
Over the years, I have diligently placed focus on creating great work that serves a large business requirement without losing touch with a deeper desire to create artistically. Of course, this has taken a tremendous effort to maintain and to suggest that the journey has been smooth would be to willfully ignore and hide from you the obstacles I’ve met and learned from.
Obstacles such as coming to the realisation, after having spent an entire year on freelance and agency work, that I was not at all fulfilled doing that kind of work (where I would see deep, creative efforts leave my domain; where control and credit over material would be traded for minimal currency). Obstacles such as my workaholic nature preventing me from seeing that my internally motivated desire to create great work was not mutually shared across the team at all and that without such knowledge I was distancing myself from people I wished to call friends.
But it is from these obstacles that I have built a strong foundation of reflective insight for which my recent and best career decisions lean heavily on. Decisions that have allowed me to access some of the greatest creative and entrepreneurial minds, providing me work in places from London to Montreal, Canada and even Foz do Iguaçu, Brazil. This is all whilst also creating some of the work I am most proud of and most deeply fulfilled to have worked/be working on…
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In moments like this, when I spend time reflecting on such incredible opportunities and the time I have had building a career off the back of them, I notice certain themes that run across these times: like a needle weaving in and out of the seams to provide a beautifully consistent pattern amongst the overall work. One such pattern has been my self-motivated insistence to create deadlines for my projects. Ranging from the side-projects worked on as a young teen, to delivering products in large tech companies as a professional today, the creation of such deadlines has proven to be a timeless strategy that I frequently turned to.
Your current project, be it a music album, entrepreneurial venture or a minor task within a larger company product, needs a deadline. It needs one more than you believe. I included that ‘minor task’ because you might not think that your current task or project will serve much long-term value and thus doesn’t require the attention required to optimise, but you’re doing the project a disservice. It is far more impactful and important than you currently know, and because of this: it too, needs a deadline.
Running home from school with great energy and speed, 16-year-old Justin was about to start his new part-time job working at an innovative tech company. The transition from a relieved feeling of completion to a re-energised feeling of anticipation had begun – for what would have always been the end of my school day, was about to turn into the beginning of my work day. A day in which my learning would come from working on things I had always been fascinated about and immensely curious toward, rather than from textbooks that had only the information that would later appear in exams, read aloud by teachers who’s focus wastefully resided in making sure the least interested students were somewhat keeping up. No wonder I was pacing home with such little care as to how I may have looked to fellow students. I was on my way to claim an opportunity that I had been presented with at the end of a nerve-racking interview the previous week.
Now, whilst I was aware my gracing with such an opportunity came from having impressed some of the fast-growing start-up’s leadership with an unusually focused and extensive CV for a teenager with average grades; there was an emotion that played against, what should have been, grounded confidence. This emotion: fear.
A fear brought about by the realisation that I was only 16, and a young looking 16-year-old at that. I thought of how this fresh-faced teenager was about to walk into a room full of experienced, hard-working professionals who had earned their way to be a high-end contributor to the tech industry. I thought of the questions those individuals would be asking amongst themselves upon my quietly-dramatic arrival:
Who does this kid think he is?
What can he even do?
Is the company now just going to start hiring a bunch of unqualified interns?
Am I going to have to spare my time to teach this guy everything I do?
Whilst I retained more relevant experience and technical knowledge than anyone my age would normally have, the rawness of these crippling doubts overpowered me. On my first day, after having met again with some of the senior members, I was sat next to the company’s lead web developer, whom for this account I’ll refer to as: John. This was a decision made to bring up my front-end coding skills to eventually help demo projects such as the one John was building.
The company I was now working as a Junior Web Developer in was Ecrebo – a, now, hugely impactful company that provide insight-based solutions to retailers amongst the likes of Topman, Topshop, Miss Selfridge, Uniqlo, Waitrose and Marks & Spencer and the particular project that I was going to be helping demo would later become one of the staple products that these retailers would flaunt. The project was, what would be later commonly known as ‘digital receipts’.
John sat me down and explained that this project was a concept piece, something that was being worked on from the sudden luxury of time made available from a slow down in work required to maintain Ecrebo’s clients’ needs. He had been working a little over a week and so proceeded to walk me through the work he had been doing thus far.
John had made progress linking dummy transactional data from a local POS (point-of-sale) system to a front-end web-interface he had coded on his heavy, Ubuntu-loaded laptop. The work he had done seemed long, complex and yet, diligent; however what I noticed, was that there wasn’t much presentable output. The front-end interface was overly simplistic for the sake of ensuring, what software engineers would call the ‘functionals requirements’ (the workings of basic inputs and outputs), were met.
Whilst I couldn’t quite comprehend every detail, John made it clear that I was not required to, but simply needed to grasp an overall understanding as my future work would come in closer contact with his more complex work. Toward the end of the afternoon, to enable me to learn more and based on the shared awareness that I was given quite a bit of information to process before resting my head that night; John shared some files from the project on my newly setup laptop for me to go through, study and to raise questions with him on anything I didn’t understand throughout the upcoming weeks.
Whilst my first day was over and I had met a lot of the faces that sat amongst the Ecrebo office, the feeling of Imposter Syndrome (the feeling that you haven’t earned your status and that you might get called on it at any moment) largely remained. I returned home after that long day and dealt with these emotions the way any non-hairy-faced-early-stage-workaholic would: I worked.
Provided by my incredible and quietly-observant mother whilst I scratched my head looking over lines of code; that evening I ate my meal (that I would usually have with family at the dinner table), at my desk. But this would prove to be a pivotal moment as whilst quickly chewing down this carefully presented and well-made dinner, barely looking at even the size of the spoonfuls, I came to a sudden realisation. The code written for the front-end interface, that was currently looking fairly bare-bones when displayed in a browser, was code that I could understand well. I recognised structural features and phrases that I brashly learned when building my first website two years prior to that moment. It hit me. I knew at that moment that I had the ability to write the code needed to complete the interface (with some creatively branded flair), giving John time to focus entirely on the rest of the project – allowing for what would be a presentable product demo for clients.
How long this would take me? Have I even got Photoshop installed on this laptop to create assets with? Am I even allowed to be working on these files?
The lack of prior experience in building such a demo provided me with very few answers. But rather than dwelling on these practicalities, like most straight-thinking individuals (who realistically would have not even contemplated anything other than what they were asked to do) would have, I began to work. Worse still… I gave myself a deadline. Oddly, knowing deep down it didn’t appear possible, I gave myself two days. That night I worked past midnight.
The following morning I woke up late for school, during which I barely paid attention in my classes – thinking and noting down various ideas for the demo: What size to make the fonts. What hierarchy each line of transactional information would have. Where to place certain pieces of a retailer’s branding. My mind was racing.
On this flow, I would proceed to run home from school again, dropping my bag, grabbing my laptop (left next to the empty dinner plate on my desk from the previous late night), before heading into the Ecrebo office.
John was not in that afternoon. What may have been expected of me upon realising this, was to turn to a different senior member in order to find out what I should have spent my time in the office working on, but instead, I sat right down and immediately opened my laptop to continue coding. Maybe it was the fact that I gave off the impression that I was working on something extremely important, but no one seemed to bother me to ask what I was working on the entire afternoon, meaning I only had one conversation on my second day at the office – and that was with the in-house designer about our favourite films. (I mean, the work I was doing was important, but a 16-year-old wouldn’t normally be given anything that important to work on. And to be honest, I really hadn’t yet, I had just taken it upon myself to work on it).
The following day I, again, walked briskly into the office and John greeted me with a polite smile. He immediately spoke to me as I sat down, “Sorry I forgot to mention I wasn’t going to be in yesterday. How did you get on? Have you had a chance to look through any of those files yet?”
I pulled out my laptop onto the desk, opened it and calmly stated: “I’ve finished the front-end portion of the demo”.
John laughed; and whilst it’s true that he couldn’t believe what I had just said – his laugh was not that of condescension, but rather, of gleeful shock. I walked him through what was definitely messy-looking pages of HTML and CSS. John and I then discussed the work required in order to complete the demo… and then did just that. By the end of the week, the demo was complete and by the following week, the company’s executive team and sales department were looking over it to find out how best it could be implemented into their next round of pitches with the high street’s biggest retailers.
Now, whilst John threw a few praises my way the day I presented him the initial interface I had built, it was a comment I received from him on the Friday after we had completed the demo that really made me smile. John mentioned how he was extremely pleased to have had me alongside him as he worked. He spoke of how I had inspired him to create a truly great early-stage product and to do so in magnificent speed. This not only made me smile, but made for an incredibly memorable start to a working relationship with John.
During my retelling of this account, you may have noticed that I did not readdress the doubts tied to young age that initially had, after my first day. This is because the doubts had actually gone.
Deeply consumed and embedded in my work, I became victim to a strategy I had deployed on myself. The strategy I used was one that my long-time mentor and friend, Adam Vickers, would later refer to as: “your ability to crush your expectations and surprise yourself”. That strategy was to make a deadline for my project. For in creating a deadline, I had diminished the time to doubt myself.
The obsessive nature driven by such a deadline could at first-thought seem like one that would go against my ability to bond with those whom I feared would question my presence, but it instead allowed me to focus on what was actually going to make a difference – the work. I had no time to think more on my fears (which were tied to assumptions rather than reality) and instead, my time was devoted to code… even then, I still had time to bond with the designer during my week’s sprint.
Now I could reveal to you what the individuals were really thinking, but that would be beside the point. What matters is the impact I actually had on those I would later get to work with, developing a reputation of a focused and determined work ethic along the way, spoken for by a reputable source within the company. What I realise now, is that the true beauty in creating a deadline was alluded to by the fact that none of these great effects were intentional, but simply by-products, rewarded along the path of actually achieving what was intentional – creating something.
Later, during my time working at Ecrebo, I would transition my role as my interest and more natural talents highlighted themselves to me. I would pivot to become a User Interface Designer rather than Developer. Whilst this meant that I didn’t continue to work as closely with John as I had done during the first few months, the beauty of having set that initial deadline for myself unveiled its long-term usefulness as all the work I had devoted myself to take on would supply me with insight into what kind of work is usually required from a developer. This gave me a level of empathy rarely embodied by those who have not worked as a developer, which I could tap into in order to build better relationships with developers – something that still pays dividends now in my career as a product manager, working closely with developers.
Already, we are beginning to discover the endlessly rewarding nature of setting yourself overly ambitious deadlines.
When I made the decision to create a deadline for myself on my first day working at Ecrebo, I chose an arbitrary number of days based on a vague assumption as to what would be overly ambitious – basically, I wanted to challenge myself. This is one thing. But reaching far beyond this is being able to make an intelligent estimate as to how long a project would take based off previous experience of similar projects or observing a well-developed status quo of an industry – then, making an overly ambitious deadline that does not at all replicate this previous, estimated number.
Peter Thiel, co-founder of PayPal and Palantir, is an advocate for doing exactly this. Whilst his book, Zero to One, often hints at Thiel’s unconventional thoughts on assumed status quo’s throughout chapters such as ‘All Happy Companies Are Different’ and ‘The Ideology of Competition’, it’s in his interview with author Tim Ferriss, and Ferriss’ book, _Tools of Titans,_ that Thiel openly presents his extremely ambitious nature.
When speaking on the founding of Paypal, Peter Thiel mentions that “If you go back 20 or 25 years, I wish I would have known that there was no need to wait.” He speaks on his time at college, law school and later his work as a lawyer and then banker, revealing that: “not until I started PayPal did I fully realise that you don’t have to wait to start something”. Thiel then presents his profound questioning-nature in the form of advice:
“Take your 10 year-plan and ask yourself: ‘Why can’t I do this in six months?’”
This task has the paramount ability to cast previously assumed convictions, about the nature of how long certain things take to achieve, into doubt.
Think now, deeply, about a goal you’ve always had in mind (regardless of whether it is a 10 year-goal or not) and then, like Thiel proposes, think long and hard as to how you could possibly achieve it in a far shorter period. In simply beginning to do so, you will begin to form a kind of calm clarity around your goal which when previously thought about, may have paralysed you with obscurity. Thiel adds a comment on exactly this, noting that “sometimes, you don’t have to actually go through the complex, 10-year trajectory. But it’s at least worth asking whether that’s the story you’re telling yourself, or whether that’s the reality?”
But whilst you may now have a detailed, yet lean action plan to execute on your idea or goal in the form of a project, you may still lack the confidence to leap into the project head-on. In fact, you may have even read my previous account of working at Ecrebo and felt that my ability to shut-off the initial, age-related doubts seem unrelatable.
Once again, this can be solved by deadlines.
My tapping into this strategy, did not originate during that first, late night working at Ecrebo. In fact, the decision was made on the back of many, many previous times in which I made the self-inducing decision to add a deadline to something I was working on. At the early age of 14, I worked on various side-projects which held my attention during evenings and weekends (probably the main reason for my pretty mediocre grades at school). One prevailed amongst the many that failed – Appfilm.
Appfilm was a website business that generated income through sponsored written content and banner/featured header advertising (and yes, this was in a time way before the dawn of Instagram and YouTube influencers). My 14 year-old self leveraged my passion for both iOS apps and movies by writing an array of long-form articles on a platform I built, reviewing content produced in both mediums. Appfilm was created for the expression of ideas I had in a time when very few platforms existed for such long-form content. Also, in building Appfilm, I was provided with the necessary skills to later read and write the HTML and CSS code to help John’s early stage demo at Ecrebo.
Throughout the journey of building this business, there were many occasions in which I relied on the deadline strategy to spur up a form of focus that would consume me. This focus would waltz me through every stress, every doubt and every form of resistance until the project or task’s end. It would provide me with the foundation of understanding that such stress and obstacles were necessary for me to see completion. This was due to the fact that my rushing would bring forward the greatly intense sensation brought upon by accomplishing something, which would supply with it: an unemotional, rational clarity needed to reflect upon that time spent executing, to see how I could improve. The many stresses and moments of resistance being the very indicators I had to study to strategise how I could later improve.
It’s important to point out that I would often fail to meet these deadlines too: from not finishing an essay to not managing to successfully pitch an advertiser to sponsor the site. But even in these moments, despite not having the same level of clarity upon reflecting, I could think back to previous successes. In doing so, I’d note that my emotion was the only thing blocking me from seeing the work needed that would actually turn my current work from a failure to success – and from here, I would work on exactly those things. (I guess it was a way of hacking my psychology to develop a similar clarity brought about from when I had previously succeeded).
For your creative endeavours, after having crossed the deadline, regardless of success or failure, reflect on your time and look closely at your stresses. Calm yourself. Remember that for any successes you may have had, the stresses and obstacles from self-encouraged pressure before then, were, in fact, essential for you to learn from, to improve upon and to gain from. Understand that they are what will move you forward and will help you create great work. From here you might start to see that deadlines not only provide inspiration for others, but will provide the foundational insight necessary to leap confidently into ambitious projects yourself.
Thus far, I’ve explained the countless benefits of creating overly ambitious deadlines for yourself. But what about deadlines for others? Can you possibly instil this same strategy in those whom you are responsible for and/or work for you? Is it even possible to evade embodying the role of the tiger parent or even the infamous ‘Seagul Manager’?
Despite the fact that my work as a product designer, manager and strategist might seem to be a likely source to tap into to provide relevant insight to tackle these questions, I am going to refer back to my time building Appfilm to hint at the possible answers. For whilst my time building Appfilm may have seemed like a lonesome pursuit, it was actually one that attracted many people to become a part of its journey.
All those who ended up helping on the business were fellow students at my school (you know, the place I attended during the time I wasn’t working on all this stuff…) and they wanted to write for the website. They wanted their own ideas, opinions and detailed analysis published publicly and realised in a similar fashion to how I had done for mine utilising my website. But despite them providing their time and efforts in order to see continued and increasing success in Appfilm’s future, I would give them deadlines to submit their writing.
How could I give them all deadlines? Did I not appreciate their gesture of wanting to contribute? Did I note appreciate the social validation from multiple sources that what I was making during my free-time was meaningful? Did I not understand that they all also had to dedicate time to homework and their social lives? Did I not care?
Of course I cared, and most definitely appreciated their efforts and time – but asking questions such as these, lazily frames empathy to a shallower nature instead of asking the deeper, more meaningful questions stemmed from such empathy. So, realising this; soon after most writers joined Appfilm, I asked myself why it was that they had done so.
I had never intended to extend the business to a multiple person operation. Those many writers came to me because they wanted to write. Or in many cases, they wanted to have written. The idea of having their work published was a realisation of what could only be a fantasy for most 14 year-olds. And in order for that realisation to occur, I had to facilitate them my platform.
So I then grasped the realisation that it was my responsibility to help them see those accomplishments through, and it benefitted every party involved to do so. Suddenly I realised that the deadlines I had always set for myself could be applied to my writers to achieve this very goal. So I began providing the writers deadlines, not brashly, but by simply explaining that I had always done so for myself, eventually agreeing on a date, whilst maintaining the overly ambitious intent.
Now there were definitely times in which some writers stopped writing. The deadlines created what they felt was an unnecessary pressure, which I could understand, especially from a 14 year-old, and so never enforced, but rather allowed them to continue at whatever pace they wanted to proceed at. However, the majority of the time, I saw incredible results. Not only were most of my writers presenting work on time, but they enjoyed doing so to the extent that they would immediately press on to the next review.
After a while, I noticed something rather interesting. Despite their first, clearly expressed desire to have their work published; the reason for their sustained yearning to finish a piece, stemmed more from the deeper, intrinsic reward and satisfaction of having completed something, than simply having their work online.
The rush. The excitement. Whilst it is a temporary feeling, it’s one that can leave permanent and long-lasting footprints along your entire career.
It is possible for you to create such deadlines for others, and whilst you shouldn’t expect everyone whom you assign a deadline, to consider your strategy the cornerstone to their success or creative fulfilment, you should expect to feel fulfilled yourself from celebrating and improving from your team’s varying stresses and wins. Plus, you’ll get to work amongst like-minded creators – and that’s a cherry on the top you couldn’t be luckier to get.
Note: whilst it is entirely possible for you to create such constraints, unlike the Seagull Manager, who flies off and leaves its trail of panic and chaos behind it, you have to stick around and encourage those working for/with you until the very end. Help them through the stresses. And if you should embody any trait of the seagull; fly high above all the stresses and have a look at what completion would look like and feel like. Then, return swiftly back to the ground and remind your troops of what they may not yet be able to see as they fight through the thick of it. To summarise: it may be necessary and even beneficial to all to create deadlines in order to lead well. Just don’t be a dick when you do it.
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Deadlines are a magnificent enabler of self-knowledge. They point to our best traits of leadership and inspiration – of our ability to impress colleagues, learn new skills and enable employees to feel fulfilled. They do exactly this by throwing obstacles and stresses at us with magnificent speed and force. And through means of repetition and constant analysis, we develop a powerful resilience. The kind of tough resilience that turns us into the cool, calm and confident artist – so we can elegantly approach our empty canvases and be sure we can handle any upcoming pressures.
So what are you waiting for? Set yourself a deadline. Be brutal. Be overly ambitious.
And, of course, create great work.
