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The Past Is Trying to Teach You
Data flows in two directions, forward and backward. The list of items we just
discussed are forward points of data. You’ll keep track of them going forward.
Backward data is just as important, though, and is a collection of information
from how things went in the past.
The past can be highly educational, but I usually don’t like to learn from it.
For instance, it took me fifty-eight long TSA lines before I invested seven
minutes into getting TSA Pre so I could speed through security at the airport.
Why don’t we learn from the past? Perfectionism tells us this is simply one
more form of cheating. We don’t need the past! That’s another crutch.
Remember, perfectionism is aggressively opposed to anything that makes our
goal easier, and learning from the past certainly does that.
It’s time to plumb your past to figure out if history is teaching you anything.
Is something you’ve already done before trying to inform your next time? This is
another one of those “don’t get lost in the list” moments. If you’re prone to
drifting and getting tangled in exercises, just answer the first three and move on.
Don’t go all perfect on me.
Let’s ask a few questions:
1. What happened last time you attempted a goal like the one you’re
planning?
Be honest here. You don’t need to shine up the results toimpress
anyone; no one else will be reading your notes. And pick something fairly
recent because we tend to misremember things the further we get from
them. It doesn’t haveto be something you finished, just something you
attempted.
2. If you haven’t done this goal before, what happened with a similar goal?
Getting on a budget might feel very different from the time you
knocked out a diet, but they’re both restrictive goals. (You’re eating less
and spending less.) There are similarities you can learn from here.
3. Who was involved last time?
I hate words like “solopreneur” because they perpetuate the idea that
you’re going to knock out a goal by yourself. You won’t. No one is truly
a solopreneur. You don’t deliver your own mail. No matter your goal,

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a solopreneur. You don’t deliver your own mail. No matter your goal,
there are going to be other people involved and affected.
4. How long did it take?
Was it a month? A week? Six months? Knowing this will help you
accurately measure the progress of your new goal.
5. How much money do you need to finish it?
Is there a budget for your goal? Money usually isn’t the first thing
you need to invest; time is, but it probably will become a factor
eventually. How much did it cost you to work on a goal last time? Did
you go over budget? Was it hard keeping track ofthe expenses? Did the
cost of anything surprise you?
6. Was there a deadline? (The project has to launch by _______)
A deadline can be one of the greatest levers to finishing. Did you use
one last time? Did it help or create unnecessary pressure?
7. Were there consequences if you didn’t finish it?
Consequences cause change. Without them, we lose focus. The last
time you tried something, were the consequences of not finishing clear?
What were they? Did they motivate you?
8. If you finished, did you get a reward?
If you’re motivated by a prize, did you get one? If you didn’t finish,
was it because you had the wrong prize? Maybe no prize at all? What sort
of reward was triggered by the completion of this goal?
9. If you didn’t finish, which part tripped you up?
Traveling makes healthy eating difficult for me. Traveling and
burritos, actually. The older I get, the more I realize that failure is
educational. When I slip, it’s important that I ask a few questions or I am
going to slip again.
10. If you could do it differently this time, what would you change?
If you tried the same goal again, how would you approach it from a

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If you tried the same goal again, how would you approach it from a
different angle?
The goal of asking all these questions and gathering as much information as
possible is to give you the greatest shot at success.
The questions above aren’t magical and they’re not the end. If anything,
they’re just the beginning of the interview you should do with the things you
want to finish. The better your questions, the better your data, the better your
odds at being successful. Please make sure you read the word “better” in that last
sentence and not “perfect.”
I know this is a lot of work, and I assure you I am doing my best to distract
you with humor and pop culture references. These exercises are as awkward as
when Jimmy Kimmel asked James Corden how much he disliked his “Carpool
Karaoke” segment with Britney Spears. Relevant!
The work is worth it, especially if you have a goal you really care about.
Keep in mind that you might realize along the way that you need a new goal.
The exercises we’re doing are nothing in comparison with the real work of
making it through the middle of a project. All I’m asking you to create is a list of
actions. If you don’t want to do that, how do you think you’ll feel when you
actually have to do the actions? Writing down “Make cold calls to potential
clients” is infinitely easier than actually doing it when the time rolls around.
Changing your goal here is not failure. It’s success! I’d much rather you
refine your goal or pick a better one than have you limp through a process that’s
difficult, with a goal that doesn’t matter to you.