Seriously, Jack needs to take a step back, look at what is happening, and reassess his situation. In light of everything that has happened, these are the things we think Jack should do next to make his life happier.
1. Go on Vacation
Jack doesn't strike me as a tropical vacation type of guy and the spot would have to be baby friendly. A nice rustic cabin, like the one Victoria was hiding out in, or a road trip to Branson, Missouri seems right up his alley.
2. Get a Will and Life Insurance Policy Written Up
Seriously, the people closest to Jack are dropping like flies and now he has a baby to worry about. God forbid, what would happen to Carl if Jack strayed into Emily's crossfire again? The responsible thing to do is make sure someone of Jack's choosing will be there to take care of his child and ensure Carl will be financially provided for until he is 18.
3. Seek Professional Help
Surprisingly, Jack has held it together pretty well despite all that has happened to him. Even the best of could use some help from time to time. Some talk therapy would help him get through some of his issues like: dealing with the death of his brother and wife, the PTSD he may be experiencing, and his obsession (and we mean OBSESSION) with taking out Conrad.
4. Take a Self-Defense Class
How many times has Jack been hurt or threatened? Of those times, how many of those situations would have been instantly diffused if Jack had used a Bruce Lee (or at least Emily Thorne) like move to scare away the would-be attacker? We're sure Jack could trek down to the local community center and sign up for one of the many krav maga, jiu jitsu, or even tae bo classes to learn at least the basics. Nate Ryan would have thought twice about messing with Jack's family again if he had received a perfectly executed karate chop to the neck.
5. Get a Hobby
Nothing takes your mind off of your troubles like becoming lost in your favorite hobby. Some people restore old cars, others take up photography. He’s already a sailor so why not branch into something completely different. Maybe take up a musical instrument?