Planning And Scheduling Vs. Creative Impulsivity

Impulsive Creativity vs Planning, Bespoke Hogaboom

My entire upbringing I was told to set my sights on something practical, something that could make steady money (you can read yesterday’s personal email, if you like), something that would be culturally esteemed. It’s all about that title, you know.

I don’t have an objection to those things. But I longed for something different.

I longed for freedom.

And every job I had – from my first as waitstaff and sandwich-maker at a lovely little sweet shoppe, to hardware store clerk to wildlife rescue worker to lab technician to engineer and foreman – I brought as much of my liveliness as I could.

And you know what, you can bring Creativity into any job! (Well, just about!) But obviously, some careers are more suited than others. The career I have today offers me more agency and expression than any I’ve had before. And I thrive in that environment! (You’ve probably noticed my energy level and my output!)

Don’t get me wrong: I am not that chaotic. I promise! I keep a rather tidy domicile, I don’t make a lot of changes to my personal style or home decor, and mostly I do a lot of writing and a lot of work with my hands! Most people would say I’m a level-headed person. I’m rather predicable in day-to-day habits. If you met me on the street, you’d see nothing particularly remarkable.

What I don’t like and can’t stand, is confining my artistry to anyone else’s expectations – in terms of style, quantity, pricing, et cetera. I never wanted to figure out what was “marketable” and then try to produce it over and over. Never liked it, never will.

A few weeks ago a professional business coach was telling me some standard business sense: that if I knew I was going to make a lot of jeans in 2022, I should buy denim as cheap as I could this year.

I held up my hand on the Zoom call and said, “Listen Jim*, I gotta level with you. The thought of committing to primarily making jeans in 2022 makes me want to lay down and perish.”

People miss the point on this. They think that because my jeans are $475 apiece, and I have a huge waitlist, I should start cranking ’em out. I could make a lot of money if I niched and ONLY made jeans. Maybe even more importantly, I might get a lot of recognition and fame – the American public loves people who pick a niche and stick to it, saying and doing the same things over and over. The American public LOVES THIS.

But I can tell you something. As things sit with me today, the idea of ONLY making jeans is not worth any price to me. At all.

Trust me. I’ve thought about this about four hundred times.

I’m sure.


Is it possible to retain full Creative freedom, and still make a living wage?

Absolutely. One hundred percent. I earn the bulk of my income from a split between design work, teaching my course (THE WHOLE ENCHILADA!), building websites for a few select clients a year, and writing for my Members. Every single thing I do, is exactly what I want to do. And each thing I do, isn’t entirely linearly related to the others! I am financially supported by a relatively small number of Followers and Members, I have no affiliateships or corporate sponsors, and I don’t pay for ads (anywhere). Perhaps best of all, I am treated astonishingly well by my clients!

I really couldn’t ask for more.

I am rather brilliant, it is true – which is why I can help you, if you want to retain me or take my course –

but also, this blog post is not really me trying to convince you to take my course or anything like that. This post is me trying to convince you that yes, an impulsive entrepreurship is possible. It’s steady work (just like any job!), but building this kind of business involves a series of learnable skills! Just like you take steps to go from sewing novice to an advanced or expert sewist – you can do the same to become an independent, ethical business!

As for planning?

Yeah, you’ll have to do some of that. For instance: I made a plan to write three days a week: my personal emails on Wednesdays, my entrepreneur email and blog post on Thursdays (that’s what you’re reading now!), and my BMC posts (for my Members) on Fridays.

That’s a lot of writing! And it is very much by design. When I was making my writing schedule for 2022 I did curb my impulsive side (i.e. almost my entire brain) to ask myself if all this writing was a smart idea. Was it a good use of my time – and would I meet this commitment?

I determined Yes to both, and I know it was the right move.

But planning to write – writing three times a week, exactly what I want to write, because I genuinely want to be helpful in these spaces – is a far cry from pumping out a business based on margins, “marketability”, corporate shilling, a scarcity mindset, and/or an exploitive supply chain.

It’s a far, far cry.

If you follow my lead, you’ll put your Planning and Commitment abilities into things you feel deeply, deeply connected to. Then it won’t be so hard to plan and to commit!

Your particular balance of Creative Impulsivity vs. Planning, will depend entirely on your values, your resources, your ambitions, your responsibilities, your strengths, and your weaknesses. (Sometimes our weaknesses need our attention! Sometimes we can gleefully own them, and avoid things we don’t want to do!) I wish I could give you more specific advice but – without knowing you better at the moment I pen this – I really can’t.

What I can tell you is that there’s a magic mixture that will work well for you.

I want you to find it. Even if you and I never cross proverbial paths again, this is what I want for you.


For a couple years of Bespoke Hogaboom I thought I was small potatoes, just funding my playtime, and this would never go anywhere more significant than that (although still an accomplishment in itself!). Then for a year or so I realized I was doing this amazing thing, and I was making good money. Then this last year I realized I was doing a really, really amazing thing, and my opportunities were growing. I was delving deeper into my Creative practice every day – while putting food on the table. Food for my family.

Now I know – to quote one of my own mentors – my Creative drive is a well that will never run dry.

Thirsty yet?


* not his name, lol


If you like what I have to share, and you’re willing to invest time in your dream – I’d love to work with you formally!

You can read more about my course here (or – get my emails).

You can read about, and apply for, mentorship here.