These days I follow this process instinctively. I don't consciously think about it. I do this in everything from marriage to Open Source projects. And, when there's a crisis or decision to make I will stop and work through this set of questions again. That's because things change and sometimes we have to as well in response. It's advice, take it or leave it. I think it probably applies to relationships just as well, but I'll focus on career choices for the sake of clarity and brevity.
Will it work?The first step to evaluating whether or not to invest yourself in a project, a technology stack, a start-up, or a community is to really honestly ask yourself if this hare-brained thing will actually work. When I interview for a job, talk to start-up founders, or even projects at big multi-national multi-billion dollar corporations I ask: will this actually work? If everything is perfect but the core idea is completely unworkable it's time to move on, no other factors (like love or money) will really matter.
It's hilarious to me that so many people trying to convince me to spend my blood, sweat, tears, and years on their project don't bother to explain to me wether their wonderful idea is going to work or not. There's usually a two sided argument to this first part of my decision making process. It's got to be a dance. The first side of the dance is the optimistic side that believes the idea, the other side is the pessimistic side that doubts. For me, I need to see that both sides have played a part in the dance. If I see only one side entertained, I'm likely to leave feeling that I've been deceived at some point. That sense of deception will likely make things unworkable later.
On the other hand, if you dwell only on the pessimistic reasons something won't work, you'll never entertain any new ideas. I was all pessimism when I reviewed Netflix in the early 2000's. I had been solicited by someone (I forget who) before Netflix's IPO and I didn't follow through on pursuing the job because all I could think of were the reasons Netflix would fail. I was terribly wrong. They succeeded wonderfully but I couldn't see how at the time, and that's a bit of a shame.
These same instincts also prevented me from taking jobs at companies that really were truly total disasters. There's a few dozen risky moves I could have taken that I won't bother listing that really would have tanked my career. So, there's a careful balance, a dance or courtship with a new idea. You have to allow for the good and account for the bad. You can't be terribly precise at this phase, but you should at least stop and evaluate in dispassionate isolation the idea first.
If you don't have the tools to answer this question, you might have to just own that inability and decide whether you're an optimist or a pessimist. Now, you're just going with your gut. At least know that's what you're doing. It's practically a defining trait of being human, we don't know things and sometimes we jump without knowing. Know that you don't know and that you're taking a leap of faith.
Answer this question from all the wisdom you have, not bravado, not fear.
Can you do it?Just because an idea will work, it doesn't mean you personally can make it work. You may not have the skills, training, or talent to make a good idea actually fly. There are plenty of wonderful ideas and opportunities in the world but if it requires a skill that you can't possibly gain there's no point in pursuing it.
In some ways, this question too comes down to being wise enough to balance bravado and fear. You are a quantifiable value to yourself. You should have done some work already in this area. Sometimes this is learning to do something a bit scary or a bit hard for you and seeing how you overcome obstacles and what trips you up.
Are you bad at math? Is math going to be key to making this idea work? Are you bad at working with people? Is this idea going to sink or swim based on people-skills? You need to have as accurate a picture as you can of what you do well and play to your strengths.
That doesn't mean you have to carry the whole project, idea, relationship, community, or whatever it is all by your lonesome. You'll hopefully have a group of others along with you for this experience. You'll need to assess whether you and that group can work together, overcome together, and if the group of you have the right skills, in the right place, and at the right time to actually pull this thing off.
Answer this question from a deep understanding of yourself and your partners in this enterprise. You don't have to be able to do it all right now, you just have to be able to grow into it. You may have to continually evaluate and adjust this part as things change.
Is it worth it?
Since, I've already mentioned Netflix, I'll mention them again. The second time I talked to Netflix was post IPO. I had a son in High School and even though I think we all thought I was a good "fit" for Netflix at the time, I wasn't prepared to sacrifice his high school and potentially college experience for my personal career satisfaction. To me, my son's continuity of community was more valuable than the amazing opportunity Netflix was potentially offering me. Part of me is wistful about that choice, but I made it knowing that my sons are the most valuable thing in the world to me and I was sacrificing for them. When I look back at it in that light I'm actually proud of the choice I made even though a potentially great future died because of it.
Most of the people I've known are great at sacrificing profoundly for something they really believed was worth it. I save this for last because it's too easy to answer blindly. A great idea might self-evidently work and the reward for making it work might ostensibly be worth it ... "we'll be rich!" ... "we'll be famous!" ... some move or sacrifice might seem worth it when viewed in isolation. The trick is, you never get to do anything in isolation.
You are always going to be you. You will always care the most about the things that you care the most about. If you don't count those things up first before you ask "is it worth it?" then you don't really know what you're selling to be able to buy this shiny new thing. I personally believe this is the source of many people's regret. They chose without knowing what it was they were doing and ended up giving up something they, in their inner most core, thought was more valuable for something that was simply not worth the thing that they exchanged.
I've known women that sacrificed family for career. I've known men who have sacrificed career for family. These people are happy or depressed depending on whether they understood the value of these trades and whether they chose the thing that was truly the most valuable to them. For some, children are worth more than billions of dollars and a place in history, for others a place in history is worth more than any personal comfort. Which are you? Which are you really? These things change.
The final question of what is worth your sacrifice relies on having answered the other two well and on knowing yourself well. If you know the idea works and you work with the idea... when all is said and done, will you be proud or ashamed of the sacrifices you made? Choose well, you can't know the end from the beginning.
Will you be proud to have failed at this?
If you're into this sort of thing, my three questions are based on the parables from Luke 14:25 to 15:32 just dressed in modern clothes and removed from the period language and concepts. It's not a complicated set of ideas. I'm sure other faiths have similar teachings, but I don't know enough other scriptures to tie them in I would love to hear other faith's teachings on this topic.
These parables in particular are about being human, making choices, and living with the consequences. They're valuable in practical ways for making us think about what we're doing and how we're living. As a collection of teachings they're an invitation to live deliberately wether or not you ascribe supernatural meanings to them.
Another analogy I've invented for this particular lesson is:
Imagine you are old and spent. There's a child you care about. You can't lie to them. You have to tell them your life's story. What will you tell them about this moment? What will you tell them you gave up? What will you tell them you chased after? Was it worth it?Knowing that you can't tell if you'll win or lose yet, you have to be comfortable discussing the loss. Live deliberately, not accidentally. Choose well, and live well.