This post is something of a follow-up to my first post in this series, which was that I think I've learned that successful professional philosophers tend "not to be shrinking violets." As I explained, one of the biggest commonalities I've seen among people who have done well in academic philosophy is that they "put themselves out there." On the flip side, the people I've seen struggle the most -- just about all of them (including myself at some points) -- shrunk away from others (from fellow graduate students, graduate advisors, etc.).
Another thing I mentioned in my first post was asking for help, particularly when you are struggling. However, although I mentioned it there, asking for help has played such a critical role in my life as a philosopher that I thought it might be worth devoting an entire post to it on its own. Let me explain why.
I can think of two real "turning points" in my career as a philosopher. The first turning point was during my ABD period of graduate school. Like all too many grad students, when it came to coming up with a good dissertation topic, I spun my wheels for a long time. At one point, I really thought I would never make it through. After a couple of years of struggling, I finally had what I thought to be a good topic, had a couple of chapter drafts, and had my prospectus scheduled. Then my dissertation committee canceled it. They didn't think it was a promising enough project. Much unhappiness ensued on my part.
What I did next was something I wasn't used to: I asked two faculty members for help. One was my advisor, the other someone not on my committee. I just asked them both, "What should I do?" As I explained in a post a long time ago, one of these people, Mark Timmons, gave me some of the best philosophical advice I've ever been given: he told me to "read, read, read -- and read stuff in areas outside of the areas you've been reading in." I did...and I came up with a topic in political philosophy (which wasn't my specialty at the time!). The other person I approached, my advisor, just expressed faith in me as a philosopher. And that was another thing I absolutely needed at that point: someone to help me believe I could make it through. And I probably never would have gotten either form of help if I had never asked.
Here is the second turning-point I recall. I was in the first year of my first job (at UBC). I didn't have any publications, and I was struggling day after day on a couple of papers that were just going nowhere. I reached out to a couple of people I'd gone to graduate school with who were (and are) doing very well in the discipline, and I just asked them, "How have you done it? How have you published so much? I could really use some advice." And they both told me the same thing. They said, "Write, and write a lot", and "Send a lot of stuff out." I followed their advice...and I began to publish. Once again, I probably would never have gotten the advice I needed if I had never asked.
Of course, I know these are only my experiences. Maybe asking for help doesn't work for everyone, or in every case. All I know is that, in my case, at two very crucial times in my career, it made all the difference in the world.