I began web design six years ago. I had seen my first website a scant 4 months prior to being presented with the opportunity to try to get a contract with the town here. I was not sure I wanted to do that - I mean, part of me did, part of me was not sure I was ready for that. I didn't act on the chance until a friend who was on the town council asked me outright to present a proposal to the council. I did so, and was awarded the contract on an ongoing basis.
I could not have known then where that would take me. It opened the door to other web design contracts, and legitimized me as a web designer. The site was acclaimed by a number of sources (and still is). I held the contract for three years before I resigned (my youngest son was diagnosed with cancer). Had I not taken that contract, my business would have taken much longer to develop the more financially lucrative service lines, and I'd have taken longer to develop a higher level of expertise in my field. The opportunity to get that contract back came again two years after I resigned from it. It came at a time when I was trying to build my business back up again - I had let it lapse while handling my son's initial chemo phases, and my daughter's diagnosis with a fatal form of skeletal dysplasia, and her subsequent death. The contract again presented me with a choice - I was not sure I really wanted it. I presented a proposal to them that included writing an admin manual for them, which my absence from the job had pointed out the need for, and for redesigning the site, followed by ongoing maintenance and updates. The contract was no longer the huge advantage to me that it had been before, but it has presented me with a few advantages I'd not have had if I had decided not to take it.
I hate council meetings. In order to get the contract both times, I had to attend many of them. I had to take the time to write up a persuasive proposal, that included educating the council members as to what the real issues where with the site. I had to track them down individually and give them the information they needed prior to the council meeting, so they would be prepared to make a decision that night. And I had to be willing to work for far less than I usually do, and volunteer a significant amount of time - When I got the contract the first time, the monthly stipend they paid was good for a new web designer. Now, my time is worth much more, and the amount they pay is hardly enough to justify my time each month. I believed the job needed doing though, enough to do it anyway. And I knew that it would help to give me a reference that was indisputable to any prospective client.