When it comes down to it, you’re hired for one reason: to worry about problems and solve them, so that your client or boss doesn’t need to worry about them or solve them. This is true of all jobs, even at the lowest level. There are some variations because some jobs focus more on the “worry” part, and some jobs focus more on the “solve” part. The lawyer, for example, may worry about the legal risks and recommend a course of action, but someone else in the company will implement the recommended changes to actually reduce the legal risk. More broadly, merely being an advice-giver is an interesting intersection between these two extremes.
This is important because the less you’re doing of these, the less valuable you will be for the company. The more you’re doing of these, the more valuable you are for the company.
This observation is good to keep in mind for every little action you take or consider taking at your job. Will this increase or decrease my boss’ worry? Will this bring us closer to a solution or not?
This has a few interesting implications.
One is that you could interpret this to mean that if something might worry your boss, don’t tell him, because you don’t want to worry him. But not telling him would go against many of my earlier suggestions, like deep transparency, frequent communication, and articulating risk factors. How do you balance the two?
Easy, that’s when the “solve” part of the equation comes in. Telling your client, “There’s a fire” isn’t nearly as helpful as telling him, “there’s a fire and as I call you with my right hand, I’m now simultaneously calling the fire department to put it out with my left hand.”
In general, you want to be open about the problems, and either propose solutions, share what you’re doing about it, or even just talk about them in a solution-oriented frame of mind.
But this isn’t just about what you tell your boss or not, it’s about what you think and how you internalize your work. The problem solver will always be infinitely more valuable than the non-problem solver, to any boss or client, unless your work is truly meaningless.
An even stronger version of this is to spend time worrying about and trying to help solve problems beyond the focus of your work. That’s when even greater value starts beyond merely just being a contractor or employee. That is the true icing on the cake. But just make sure that doing that doesn’t come at the expense of your core work.
Finally, note the difference between “solving problems” and “recommending solutions.” For certain roles or jobs, your job is merely to make a recommendation, like the lawyer in the above circumstance. But for almost all work, your job isn’t just to make the recommendation but to either make sure the solution happens or help make the solution happen. You don’t want to hire a designer who says, “we have a problem, the new web page is ugly and unlikely to be effective” but the one that says “we have a problem, the new web page is ugly and unlikely to be effective… and here is a mockup of a design I did that I suspect can solve both of those problems.”

