Bullish Q&A: How Far in Advance Should You Plan Your Career?

I own a small business – a one-woman [alligator wrangling] consulting firm. On occasion I do hire additional help on a contract basis, but usually it’s just me. I started the business four years ago and have been pretty successful. Summers tend to be a little slow. I plan financially for slow periods so I’m okay in that regard, but after a week or two of decompression I feel… lazy? Bored? I live in an outdoorsy town, so there’s plenty to do – hiking, cycling, etc. – but my brain needs to work too.

I’m debating starting a second business. It would have to be very flexible so if good work becomes available in my current business, I can take it. I love what I do so I don’t want to dial that back at all but it often requires travel. I can’t be tied to a second business here in my town.

I’m also thinking if I were to plan 2014 better, maybe I could plan this slow period right out of the schedule by stacking business in the summer. I don’t mind some time off – I have an insane schedule for most of the year – but two consecutive weeks is all I can handle. 🙂

How do you make decisions like this – working to grow an existing business versus starting a new business? I saw your discussions about “retreats” where you plan the next year. How do you plan an ENTIRE year? I plan a few weeks or a month in advance at best. (This is also why I’m not married – commitment – EEK!) I don’t really care if I have a second business. I can see benefit in “diversifying”, but mostly I’m seeking to even out the peaks and valleys. Or should I just plan financially for the valleys and take my dog to the park more?

– Wrangler

Great question! And I certainly don’t mean to create unrealistic planning expectations (more on that below).

First, I checked out your company website and blog, and I’m impressed. Four years is relatively new for a business, but long enough to get a handle on the seasonal nature of the work.

Yours is certainly not the only profession where summers are a little slow. (While the tutoring world slows way down in summer, I am discovering that the luxury cat care market picks way up!)

I answered a question here from a reader in Bullish: Where to Get a Kickass Business Idea, in which I suggested ways to think about catering to tourists, which seems appropriate to your need for a summer-centric business.

So, some of your options are:

1. You could start a business that does most/all of its business in the summer. (Isn’t there a way you could tie in your new business to your current business? Aviation summer camp for kids?)

2. You could start a business that doesn’t slow down in the summer, and then play both businesses off each other, generating enough work that you can raise your rates. Then you’re making more money for the same amount of work, and you can pick and choose your projects. There’s nothing wrong with being so popular that sometimes people can’t get what they want.

3. You could develop a gentlewomanly philanthropic, athletic, or educational pursuit to occupy your free time. Keep in mind that you have not only free time available, but *energy*, which is important (you say you’re too restless to take more than two weeks off). For instance, you could raise money and then go to Ethiopia to build a school. Or, you could ride a bike a really long way to raise money for AIDS/HIV research. Or spend some time on a wildlife preserve. Or you could take cooking classes. None of this is mutually exclusive with #1-2. Some of these things are good PR for you as a professional. And trying something fun and random — and meeting the kinds of people also doing that fun and random thing — is a great way to generate business ideas.

4. You could use the downtime to improve your business. I know of one coach and speaker who produces an entire year’s worth of blog posts and podcasts in one focused, six-week period every year. Would you be able to bill more, consult more, market more, network more if a whole bunch of the BS were already taken care of? You could certainly write 26 blog posts over the summer, and then release them bimonthly on your blog. What if you just took a week to get all the accounting, insurance, and regulatory paperwork done as far in advance as its possible to do it?

5. You could, as you say, plan 2014 better so that business gets pushed and pulled into the summer lull — kind of the aviation equivalent of the local bar’s “Ladies Drink Half-Off on Mondays!”

How does one plan for an entire year? When I said I was doing that, I think I may have been using the word “plan” a bit differently from how most people use it. What I did in a Vero Beach hotel for two weeks was more like: Go over my to-do lists. Make more plans. Read some books. Make even more plans. Think about the plans in a relaxing environment and try to form a coherent picture of what it would really be like to pursue (all, or most, or the best of) the plans. Figure out what to do first. Get started.

(See Bullish: How to Have a Staidcation.)

Two weeks of planning in December tells me exactly what to do through about February 15th. After that, it’s responding and resetting and refining, as always.

The only people I’ve ever seen make a really detailed plan and actually stick to it over a long period of time are people who are pursuing one extremely well-defined goal, usually within an institution, where the stepping stones and procedures are also well-defined. For instance, if you want to be an astronaut and go into space, there’s a pretty clear path to that, albeit a lot of competition.

I think that kind of planning might be appropriate when there’s something big and hard that you definitely want to do, that takes a limited amount of time (a year, for instance), and that you’ve put off for some time. If someone decided it was finally time to lose 75 pounds, or get a book written, then that kind of planning might be appropriate. For most people, maybe one year out of every ten should be planned like that.

But most of the women I talk to don’t want to do just one thing, and want to define their own paths. And there’s an opportunity cost to rigorous planning and diligently sticking to the plan: when you have tunnel vision, you just don’t see new opportunities.

I think the way you plan is fine. After all, you don’t know when your clients are going to call and what they’re going to want, right? You can work with your natural commitment-phobic impulses.

Since this summer is already in progress, why not survey yourself once a month?

What would you rather be doing: Working on a new business? Pursuing a new skill, philanthropic project, or adventure? Gearing up for September, making 2014 run more smoothly?

Rather than far-out, speculative planning, sometimes we do better collecting data, even if about ourselves.