I quit my job in early 2013 to do my solo start up. I'm still developing the product today. I'm not sure if the following story/advice is good, but it represents my experience and ultimately shows how I managed over my hurdles.

After quitting my job I set all kinds of expectations on myself. None were reasonable. Every time I had coffee with friends or past colleagues I would get asked how well I was doing and when I might be complete. From day one I felt pressure to achieve some milestones and when these questions came up I inevitably declared unrealistic targets. Worse, after I declared these targets I would feel like crap as began to realize I was nowhere close to meeting them. It got to the point where I would just stop working.

At one point, I stopped for 2 full weeks before deciding to face up to the truth: I obviously wasn't prepared for what I had decided to do. I was failing...

I then realized that even before I quit my job I had been in the habit of biting off way more than I could chew. See, these big corporations I had previously worked for had instilled some really bad habits. They would intentionally give employees more work than they could actually handle, with the idea that they were challenging their employees. No big surprise that every year the performance reviews would tend go the same way. Managers would identify with all the achievements and show understanding on initial goals that were not reasonable to begin with. It makes the employee grateful to manager for the big bonus and also makes the manager out to be a keen observer with great understanding. Certainly fosters a good relationship. The downside in all this is that they establish a really bad pattern/behaviour to have unreasonable goals with reasonable outcomes. I'm not going to get into the good and bad of the practice suffice to say it didn't help me when switching to a start-up. In fact it made me feel like shit along the way.

So I decided to stop and made a huge list of all the obligations in my life, and I mean everything. From family time to shovelling the snow, mowing the grass, and paying the bills, but more importantly I then prioritized them with a cost ranking. I discovered something interesting. It turned out the things I perceived as small or insignificant we're consuming large portions of my thinking time. While they would only take a very small amount of time to deal with, they had a big 'nag-effect' until they were done. For example: doing taxes. I spent months with background thoughts focused on my changed situation and wondering how optimize any re-situated tax implications. This item was always way down on my list in importance and should have been much higher had I understood myself well enough to identify it was costing me more than I realized.

I continued on by spending the next two months really simplifying my life. I took my list of 100+ ongoing obligations and reduced it to 10. ONLY 10: ongoing.

Afterwards, I got back to work and became really productive. These days I make sure I set small goals with really lofty timelines. I'm pretty sure some people will find faults in this new practice, as I can see obvious faults myself, but that's ok. I'm now the happiest I've been in 10 years and I don't fall into anymore motivational ruts. Week by week I'm consistently happy with my accomplishments and for the last 5 months or so I've maintained enthusiasm with almost everything I do.

So I'm not sure if this is helpful, but here's the advice:

Allow some time for understanding who you are and how you best operate. It's really important to get your head in the right place, before you start and along the way as you observe problems. Be aware of your thinking patterns and don't be afraid to make really big changes if that's what is required to get you there. Only set timelines that are reasonable to accomplish. Review all timelines/expectations and spend some time trying to call bullshit on them.