Dh and I are and always have been stable average lack of imagination people.
We met at school , went to uni, got married, worked had kids and started our own company in a very careful way 
Our relationship is wonderful we have 5 (nearly 6) beautiful children and yet we both know that our caution has caused us to miss out on so many opportunities.
We are living comfortably BUT each month is a stress and a struggle because we earn just enough, so no savings, no home of our own (we rent) and no car either (avoiding paying out more than we can afford ).
At work we know that two of our employees take more money to keep than they actually earn but again we are stranded in a sea of what ifs!
Dh alone earns more than enough to support us but he ends up using what he earns to cover wages and rent etc.
We have both been dancing around the idea of change for example dh working from home on his own and getting rid of the company totally BUT we are hampered by a total lack of imagination.
The most important things are dh works 14 hour days ATM which is a little much and we would love a house or some sort of permanent place to call our own.
I'm not crazy am I being careful and doing the "right" thing is not serving us well us it?