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.

Read the rest of the post over at Bullish!
Read the rest of the post over at Bullish!

Share This Post: