How to UpWork

how-to-upwork.md

How to UpWork

1. Write everything. Regardless UpWork or current amount of projects. Tasks, plans, meeting notes, requirements, questions, whatever you have. No need to keep this stuff in your head.

   Specific tool does not matter. I'm using plain text files in Dropbox for work notes, email drafts, and any other texts. And A4 squared paper notebooks. I like paper because it is fast and dead simple (and because I like handwriting). But this is a matter of personal preference. Just try different options and see what will work.

   And try using some task tracker if you don't do this yet. Even for your personal notes and planning. It really helps to keep things organized, when each task has a timestamp, there is full-text search, and you may see the list of what was done today, yesterday, or this week.

   I like trello.com (super-simple way to organize lists), checkvist.com (minimalistic general-purpose outliner). Some of my friends like Todoist, a nice organizer with mobile client. There are gazillion of alternatives.

2. Make your work transparent. Try sharing your notes with the customer or team. Don't wait when they ask you about your progress. Just update regularly and proactively, instead of on-demand. Push is better than pull here. This way you will have lower chances to stuck on something. And higher chances to figure out events affecting your further work (changes in requirements or priority, misunderstandings during task definition, etc).

   By doing regular updates you may prevent routine questions, interruptions when you working, and sometimes even unnecessary meetings. (To be honest I don't like having status meetings in a middle of working day. They are really distracting. To me it takes up to half an hour to switch from "meeting" mode to productive mode where I can work again. But YMMV.)

   Another benefit from regular reports is that it work like a small milestone. Between weekly iterations helping to do a reality check and planning adjustments. When you doing reports, you have history. And using history you may track things, see what was done, how much effort it took, etc.

3. No more than 1 project where responsibility is high. Meaning, when I already have a project with high demands (for example, it requires significant amount of hours every week, or response time is critical, or there are daily meetings), I prefer to avoid having others with similarly high responsibility, regardless if there is seemingly enough time for both.

   It is OK to some people to split time/cognitive resources in proportion of 50/50 (or 33/33/33 if there are 3 projects), but I've noticed that to me proportions like 80/20, or 70/20/10 work better (one primary projects, 0..2 secondary projects). Otherwise it feels very distracting just to keep in mind 2 contexts with similar weight.

   Switching between project has non-zero cost, and your total productivity is inversely proportional to the amount of these projects, and the intensity of switching between them. So less projects and less regular switching → higher productivity.

   If there is a big ongoing project, my preference is to dedicate whole day or 2-3 days in a row to it every week, instead of splitting working hours every day between multiple projects.

4. Mind the risks. Amount of required work on any project could vary from week to week. For example, something important may come up unexpectedly, with priority level "has to be done yesterday". Other projects should not suffer because of it. For this reason it is better to keep some extra time reserved.

5. Be careful with your estimations, and avoid doing them unless you need to. I systematically underestimate things, at least a little. Underestimation is usually caused by common cognitive distortion, and there are many reasons for this (in short, most people are terrible at foreseeing future).

   Just try to remember that actual amount of effort is usually higher than expectation. And what people call an "estimate" is actually just a guess, not a promise. It still could be a good guess, though. But if a customer use your estimate as a promise, it is a bad symptom.

   So underpromise, overdeliver. Try not to overpromise just to be a nice guy. And if you unsure about timeline, it's better to say it aloud right away.

   When you can't estimate something (but you need to), try to postpone it till the moment when there is enough information. For example, take couple of hours for research, or just start working on the task. Usually it becomes more clear afterwards.

6. Remember about priorities. Sometimes it is very easy to spend all time you have doing less important stuff, but miss what was the priority. Even (and especially) when you know about this importance and relative complexity. Unconscious switching towards easier tasks is based on the same mechanic as procrastination.

   Make it a habit to keep asking yourself from time to time: am I doing the right thing, or there is something more important? It helps.

7. If you feel tired, just go and have some rest, or call it a day. Working when you tired, or sleepy, or don't feel very well is counterproductive, Especially when the contract is paid on hourly basis. It is usually better to spend 1 hour resting, and then 1 hour working, then 2 hours kind'a working if you tired.

   And there is a danger of burning out. So figure out your work-life balance, take vacations from time to time, don't try to work in 24 by 7 mode, don't forget to eat and sleep (no jokes here, it is actually very easy to forget about dinner, which is unhealthy and inefficient), go outside regularly, do some sport.

8. Keep calm. In my case this one should actually be number 0, because it is a dependency for everything else. You are wa-a-ay more productive when you not in rush.