Good for you for starting to ask the right questions.
Keep in mind that, as previously pointed out, there are more than two answers to every question.
For companionship, can you volunteer or join a club? What about attending trivia night at a bar/restaurant every week? You'll get to know the regulars. Do you have buddies who like to hike, play board games, fish, etc? Maybe you can have pot-lucks every now and then too and meet their friends and neighbors. Does your neighborhood have a community center? If you meet a special lady that's great, but you will definitely meet some good friends.
For winters, do you have friends or family in sunnier places you could visit for a few days here and there? Have you considered using a light box?
For work, do you know exactly where you stand with your finances and how much you need to make to support yourself? Or are you already at FI? If so but you still like what you do, consider raising your prices or only doing the jobs you really like. Our handyman won a lottery here and still works, but now won't do drywall because he hates it. He'll do wiring and painting and other stuff that he likes.
For travel, start with visiting people you already know or places you've already been, or start with short day trips and graduate to weekend road trips. If those go well, you can branch out more. It's even better if you go with a buddy.
Hi Julie, thanks for your reply.
I have something that I do regularly.. its social dancing and I like it, and I know people there and can say hi and how is this and that. But considering the amount of time I've been going there it doesn't really seem to equate to much.
Vancouver is where I'm living, and it has a reputation for being cliquey and hard to meet people. I have to say I think its the case here.
I was thinking just today that its not always a good thing to dwell on my own personality to much and question what I should or could be doing better... I have a hunch that just move somewhere else and 'hey presto' suddenly problem solved and friends a plenty.
I might have a look around and see if somewhere else feels like a better fit.
There's a community centre but its a bit of an anonymous place, not the kind of place where people will say hi and remember you. I think thats the thing living in this city, I go outside and its a lot of high rises and lots of people, but can walk for hours and not see anyone you know.
Im on top of the finances, I think I'm doing good in that area.... probably what has happened is that over the last 10 years I've had to deal with a lot of very heavy family situations, while at the same time having to take care of some hefty financial responsibilities.
Things worked out financially and now I'm 10 years older and need to focus on things other than working. And as Mozar said earlier, I think I've got a lot of anxiety going on in my thoughts... I think I should make dealing with that a priority.