Based on my suspicions, Alamak's professional and personal future are "best" when Jupiter is traversing through Sagittarius, Pisces and Cancer. It's not doing so well when it's travelling through Gemini, Virgo and Capricorn.
Career/Future was Supposedly Doing Well
Jupiter in Pisces
- February 1998 to February 1999 - Alamak completed his GCE O Level exams in 1997. He started and dropped out of high school, enrolled in a vocational college, dropped out of it and returned to high school in March/April 1999.
- January 2010 to June 2010, September 2010 to January 2011 - He started a new job in January 2010. He was very valued and appreciated in the new company.
Jupiter in Cancer
- July 2001 to July 2002 - One of the best times in his life. He was assigned to an army in May/June 2001 unit that he doesn't mind.
- June 2013 to July 2014 - Alamak started an 3 or 4 month contract in June (or July) 2013. He had an offer to extend his contract when the initial contract ended. He wasn't happy with the offer and declined it. He subsequently received two very attractive offers and accepted one of them. However, he didn't do well in the new position and was at the risk of being terminated in May 2014.
Jupiter in Sagittarius
- November 2006 to December 2007 - He switched departments in January 2007, was assigned to the worst manager in the department, stood up to her in mid-2007 and was assigned to other managers since then. The former manager badmouthed Alamak and nobody wanted to take him up until January 2008 when another manager had to due to resource constraints. [Note: Alamak's career certainly wasn't doing well during this time. A look at transits, progressions and directions may be warranted. Okay, a quick look indicates that transiting Uranus was stationing and conjunct his natal 10th house cusp during this period.]
Career/Future was Supposedly Doing Not Too Well
Jupiter in Gemini
- July 2000 to July 2001 - He took his GCE A level exams and was enlisted in the army in early 2001 which he found incredibly tough.
- June 2012 to June 2013 - Alamak was unhappy in his job and researched other career options. He had a depression and was very vulnerable. He left his employment in October 2012, took a career break and started another in June 2013.
Jupiter in Virgo
- August 2003 to September 2004 - Alamak started college in July 2003. His results were okay, not spectacular.
- August 2015 to September 2016 - Alamak confided to me that he was getting nowhere in his career. He was looked over by his superiors for important projects and landed the insignificant ones. He managed to secure an employment offer with another company but eventually switched department within the period.
Jupiter in Capricorn
- December 2007 to January 2009 - An extremely tough and challenging time in his career where he worked 80 hour work week for six months and 60 hour work week otherwise.