I’m a 45 year old business owner who also has focussed on diversifying my income streams. I have a short term vacation rental in Florida that I bought for $390k in 2012 and net rental income for the last three years has been growing steadily. 2015 I am at $70k gross right now but should end up at $80-85k with net around $45k plus we use the place about 35 nights a year.
I’m looking at accepting a professor job. It’ll be more than a 50% pay cut. But I’ll have the same life you describe – endless summers and an entire month every winter to ski. I’m thinking in the end, eventually, I might even end up wealthier in more ways than one. Happy people tend to be the most successful. I have no desire to diversify. Dividend stocks allude me. CDs seem like a good choice for older people, but I have time on my hands and real estate knowledge, so I’m sticking with what I know, despite the fact that most people will tell me it is foolish and I should diversify.
I knew I didn't want to work 70 hours a week in finance forever. My body was breaking down, and I was constantly stressed. As a result, I started saving every other paycheck and 100% of my bonus since my first year out of college in 1999. By the time 2012 rolled around, I was earning enough passive income (about $78,000) to negotiate a severance and be free.

Regardless, it took me around 18 months to start turning a profit online. It started with around $100 per month, then grew to $200 per month. Then it kept growing and growing until, eventually, the money I earned online surpassed what I earned in my regular, 9-5 job. That was last year, and my online income is still growing. Believe it or not, it all came from starting this simple, yet effective, blog.
Ancillary Activity Test - The nonresident’s presence in Connecticut is ancillary to his or her primary business or employment duties that are performed at a base of operations outside of Connecticut. Ancillary activities are those activities that are secondary to the individual’s primary out-of-state duties, and include such things as presence in the state for planning, training, attendance at conferences or symposia, etc.
In focusing on your wealth management goals, investment income is obviously critical but you might fund your goals from wider sources of income.  A typical long-term portfolio might produce about half its return as income and the other half as capital growth, though in times of duress the capital growth component wanes.  In this low-interest rate climate, some sources of income have become quite expensive and may prove disappointing against your spending needs.  But by tax efficiently and sustainably drawing income from wider sources, you might meet your goals while more prudently balancing risk against reward.
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