My partner struggles with pessimism, usually caused by focusing too much on the work ahead and too little on what has been accomplished. One technique we've found that helps is to keep a "done" list, separately from the "todo" list. The size of the todo list can be intimidating, but having a separate list which only records accomplishments that you can look over when you get stressed to remind you of just how much shit you've got done. From the perspective of a team, this could just be making sure that you spend enough time celebrating your wins.

I also find this challenging. One thing I can suggest that has helped me on my current project, is to do a morning standup. It's always brief but I use this time to set a mood/tone for the day. I try to lead with something relevant for the team or business, hopefully good news, but still try to motivate with a sense of direction towards what we're working on and where we're going. We'll each give our status and have an opportunity to bring up blocking issues, successes, or anything else. But I've found that my team looks for this ritual to assess my mood. I try to stay optimistic towards the effort, our business and the opportunities we're all working towards. When it gets slightly frustrating on a day to day basis where the "business" side may not be meeting the "engineering" side, I try to make dry light humor where we can laugh a bit during standup knowing that we're pointed in the same direction. Not an exact science, but on the day to day, try to find something to laugh about. This usually finds people willing to pair up together to take on "the cause" or whatever the team needs to get done.

> One thing I can suggest that has helped me on my current project, is to do a morning standup

I've found that this is the only sane way that works if you're trying to manage a team of 15-20 people.

15-20 people is 2-3 teams in any sane organization.

I find that pessimists miss a critical factor a lot of times.

Things that are empirically bad are just going to suck.

Things that are just "hard" are going to suck too.

In business RARELY are things actually bad (site outage, layoff) and often just "hard" (I need you to work late).

When things are hard you can say they are HARD and let them be HARD and use the occasion as a chance to create camaraderie. Stuck late in the office, then start singing show tunes badly - bring in food and beer (if appropriate) or good coffee the day after - hard times build great teams if they aren't "every day"

Find a things to have with your team to make it more entertaining - I worked in an office that ran on the back of quoting film, and there is a film quote for EVERY situation. A good friend of mine works in a "nerf gun" office, and I used to work in a place where "team lunch" was a thing that was sacred (you would leave every day for an hour). Alone these things don't do much but when it is HARD (or bad) the activity restores a sense of normalcy for you and your staff.

Be honest about hard, sometimes you just need to STFU about bad (layoff).

   I find that pessimists miss a critical factor a lot of times.

Optimists miss critical factors all the time also. Which leads to all sorts of problems with expectations.

I think the real answer is to be optimistic about people, but realistic about projects.

You are right about hard vs. bad, but it's also worth noting you have to be careful about pushing your own ideas of team support. When you are asking more of people (stay late) it's worth thinking about what you can give them that they want, not what you envision. And if it gets really HARD, think about how hard you can advocate for getting them something material after (promotion for performance reasons, extra time off, a situational bonus, whatever)

I too like to dwell on the negative side. When you're the boss everyone really is looking to you so it is important to keep everyone's morale up.

Hopefully by the time you're a manager you realize the grass isn't perfectly green anywhere, and every team has good and bad points - remind everyone of the good that is happening. Maybe you have to start policies that people will like ie interesting tech or tools. Even if things are going badly you can have team lunches or drinks that are non-work related - it really helps team spirit.

I find that the biggest intellectual mistake of pessimists is that they take an actuarial view of reality: "99% of startups fail, thus we are doomed from the get-go and our <current problems> are evidence of that".

This might be correct if you take a 3rd-person perspective view, but ignores human agency and the ability to steer situations - sometimes via sheer willpower.

See Paul Graham's essay on Intellect vs. Determination.

It's a lot easier to be optimistic about a product you actually care about in some way.

Savor the small victories.