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Planning Ahead: 3 Lessons I’ve Learned The Hard Way

Time

Planning ahead. It may not be the sexiest topic when it comes to business mindset and strategy and yet, it’s one of the most important things. Without plans, how will you know what you’re supposed to be doing each day?

When I first started setting my own schedule (versus my boss telling me what to do), I found that I would tend to float. I’d spend way too much time fiddling around on one project and not enough on another. I also thought butt in chair was equivalent to working, so I’d glue myself to my desk for eight hours.

Oh how unproductive some of those hours turned out to be!

I learned the hard way to take a little time to plan ahead. It’s the smartest move you can make in business to maximize your time. Here are three mistakes I made and how I learned effective ways to plan ahead. Hopefully you can catch yourself so the areas that tripped me up won’t get you, too!

Rigidity Killed The Cat

I love doing the same thing every day, as my CEO schedule mandates. Not having to think about what I could do and instead, opening my calendar to see that my EVA, Sadie, has scheduled a work block or that it’s Tuesday and that means I coach all day is so freeing to me.

That said, getting into the mindset of, “This is the way and it has to be this way,” can really hamper you, especially if you’re a creative entrepreneur. Rigidity in this sense can close you down to seeing new options and ways of working that may be better for you and your plans.

When planning ahead, I always have a loose plan. It allows me to know what I want to accomplish in my day without shutting myself down to new possibilities that come to me.

For example: Having a work block at 1pm is a loose plan. I know that I’ll be doing something, but I haven’t said exactly what. That allows me to have time and space to take care of needs that arise and batch them together in that work block.

Success Tip: Adopt a mindset of rigid flexibility.

Sometimes, my gals get tripped up when starting something new. They like to plan things out and get caught in thinking, “This is the only way it can ever happen, so I have to do it right from the very beginning.” Like, they must go to the gym at 6am and that’s the only time they can exercise for the rest of their lives, so it better work!

(I know, I’m using a bit of hyperbole to highlight my point. But you get it, right?)

My clients know that my favorite answer to, “How do I do X?” is, “Rigid flexibility.” Rigid flexibility allows you to hold space for your plans, but not get too precious about how things get done. You can set a schedule for a while, assess how it’s working out, and change the plan when you need to.

The ability to adapt and be flexible is one of the most crucial parts of setting plans. It’s great to plan ahead and know what your day will hold, but avoiding getting started because you’re waiting for the “right time” is a sure-fire way to halt any progress.

Business Plans Are a Waste of Time

How many blog posts have you read when you were starting your business that said, “Have a business plan!” They went on and on about how a business plan is the first thing you must have as an entrepreneur. You think that you’re planning ahead and setting yourself up for business success.

Here’s the thing: You could spend hours and days on a business plan. Then, you get one great idea that pivots your business and your plan is totally obsolete. All of those hours and days spent crafting the perfect business plan are totally lost.

Trust me, I know that gut-wrenching feeling. My first time creating a business plan looked something like what I just described. I didn’t allow myself the option to pivot when I got a new idea.

So, I’ve opened up the idea of creating something that’s more flexible. Instead of making a rigid plan based on an assumption of how something will work, I allow myself to try out a new concept. Every time I try it, I inevitably learn something new that goes into the next iteration.

Creating a business plan is like entering into a constantly-evolving relationship. You’re never the same person; you get to change and does your business. Essentially, creating a business plan is committing to a relationship with your business. You learn new things about yourself and your business.

When planning ahead as solopreneurs who get to call the shots, having a loose structure of what you want to accomplish is helpful. But, hell, your “business plan” could be scrawled on the back of a cocktail napkin while you’re having drinks with your biz bestie!

Know that your plan will change from month to month. And don’t get wrapped up in the details. 

Short-Term Planning is The Best Planning

During a recent trip to Florida, I was completely on my own for a day. This was like ambrosia to my mind and I wanted to do something fun with my time alone. It felt like this: I could do so many things! Where do I start?

So, there I was on the plane, planning out my next few hours at Disney.

(I know, usually people plan a trip to Disney months in advance, and I do, too; however, I’ve been there so many times, I can literally pull up in an Uber and know where I’m going.)

This time, though, I didn’t have any kind of structure or short-term plan. At the end of the day, I barely “accomplished” anything. I didn’t ride or eat. I did walk around and have a good time. But I didn’t check anything off my list. And I was exhausted because I wandered all over like a Family Circus cartoon.

If I had gotten off the plane with an organized idea of how to approach my day, I could have known that I would visit X, Y, and Z. Then, after getting to Z, I could check in with myself and plan the next bit of the day.

Success Tip: Ask, “How am I going to craft the day tomorrow?”

Take a few minutes at the end of the day to plan ahead for tomorrow’s activities. Come up with a structure that will allow you to accomplish your “must dos.” Then, build in time to check in with yourself. Assess how you’re feeling and how else you can maximize your time and enjoyment.

Having a short-term plan laid out a day or two in advance prevents you from feeling like you just ate some snacks and wandered through your day.

Are you someone who likes to plan ahead? Did you learn these planning lessons the hard way or have you always enjoyed structure and knowing what your day holds?

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