We understand that there are some people who aren’t excited about planning - some people for whom the very idea of planning seems like a restrictive chain, holding you back from creativity, freedom, and achievement.

Other people are just too busy for planning. There’s so much going on right now, who has time to map out the future? And, really, is it even worth it?

You don’t even know how alien these ideas are for us but, since one of us is a financial planner, we might be a little biased when it comes to this topic. However, that bias is well-earned - we know planning works.

Planning of any kind - business, financial, personal - actively creates success. The truth is that creating and making use of plans (reviewing, updating) actually improves whatever aspect of your world that you’re working on. Whether that’s making your business viable and sustainable, building a retirement or buying a home, or just figuring out where you’re taking this life you’ve got, planning really, truly works.

While planning improves your likelihood of success, it doesn’t have to be boring, and it doesn’t have to be restrictive. Remember that a plan is simply a map. It’s not a cage. It’s a guide, and a pathway. You may take detours - but you know where the main road is, and you can judge how far you’ve gone.

Want to be even more successful in your planning?  Don’t do it on your own.

Here’s why:

We humans are an optimistic bunch. Sometimes, that optimism can bite us in the ass - and those bites go really deep when it comes to planning.

Our optimism makes us really bad at estimating anything that we do ourselves. All of us. You’re not special (well, you’re special, but not in this specific way). Whether it’s how long a task will take, how much it will cost, or the gain you’ll enjoy from getting it done - if you’re the one doing it, you are going to underestimate the work and overestimate the benefit.

Even familiar tasks that you do all the time. Even tasks you’ve done before.

Don’t feel bad; every other human on the planet has the same biased approach to their own work. It’s actually called the “planning fallacy” and you can read more about it here.

Here’s the really interesting part: “The bias only affects predictions about one's own tasks; when outside observers predict task completion times, they show a pessimistic bias, overestimating the time needed.” We clearly think that other people will take much, much longer than we would ourselves for the same task. In reality, we’re better off estimating someone else’s time for them, and having them estimate our own. It’s why we need that second set of eyeballs on our plan.

On a related note, we also tend to overestimate what we can accomplish in the short term and underestimate what we can accomplish in the long term. This means that if you’re only ever looking at the short term, you’re bound to be disappointed. Focusing on the long term, and frequently doing better than you’d estimated, will only improve your mood, and motivate you towards greater success.

“We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten. Don’t let yourself be lulled into inaction.”
— Bill Gates

Realistic planning: steps to creating and sticking to your plan

  1. The first step of realistic planning is knowing how much time you actually have to work with. Your time is, of course, affected by things outside of your control. But just because you can’t control them, doesn’t mean you can’t plan for them. Start with a year-long view of your calendar. If your kids will be off of school for 2 weeks for spring break, put it in the calendar. Birthdays, anniversaries, graduations, vacations - all of it goes in the calendar. Be realistic about the fact that you will need to spend time with your family and your friends during these periods, more time than usual, and plan for it.

  2. Set your goals for the year (or even better, the next 3-5 years). These can include:
    • Revenue
    • # of new clients or customers
    • Projects like launching a website, opening a new location, investing in equipment or hiring staff

  3. Break your goals down into quarterly targets. Bear in mind that if you plan to take any vacation time (and yes, you need to take vacation time), then you’ll need to be more productive in the quarters that are not affected by vacations and seasonal trends. One of the big reasons that entrepreneurs burn out is that they fail to build rest periods into their plans. And then summer comes around and they haven’t hit their targets and they think “I couldn’t possibly take time off now!” This is why completing these steps in order is so important. Book your time off first, then set your goals, then start mapping out your quarters.

  4. Once you’ve got your quarterly targets, break them down by month, and then by week. As with the quarterly targets, your monthly and weekly targets will be affected by holidays, long weekend, visiting in-laws, whatever.

  5. Review your goals with someone else (remember what we said about estimating your own timelines?)

  6. Set a reminder to review your goals weekly, quarterly, and yearly, ideally with someone who will help keep you accountable.

  7. Celebrate your wins. It will keep you motivated to stick to the plan.

  8. Importantly, be flexible to change. Remember, your plan is a roadmap, an outline. Life will come along and knock you off course. When you manage to pick yourself up, wipe the dirt from your hands, and start walking back, it’ll be handy to know where you left off, and where you can jump back in.