Change Catalyst with Shanna Mann: Strategy & Support for Sane Self-Employment

≡ Menu

Advice for People ‘Living the Dream’

  1. Your Emotions Have Something to Tell You
  2. My Art Is My Business– And Now Both Are Stuck!
  3. Advice for First-Time Entrepreneurs
  4. Q&A: How Much is Too Much for Professional Development?
  5. Advice for People ‘Living the Dream’
  6. How Do I Make Good Decisions about Investing In My Business?
  7. The Non-Skeevy Way For Introverts To Make “Friends” Online
  8. “How do I get to know people without feeling competitive?”
  9. “I need to charge more. Is this a valid reason to raise my prices?”
  10. Q&A: The Fundamentals of Growing Your List
  11. Where Do I Spend Money on My Microbiz Until It’s Successful?
  12. Q&A: How Do I Know When I’m Making Enough Money To Hire Help?
  13. Q&A: When Will It All Hang Together?
  14. 3 Times When You Don’t Have To Answer The Four Questions (and 1 Where You Do)
  15. Help! A Client Called My Bluff! What Do I Do Now?

My irregular advice column returns with this question:

Abby Markov writes:
I was poking around Audible looking for a book to use my monthly credit on, and was checking my usual categories: Business, Inspiration, Motivation – and the likes.

I saw a metric ton of books on working out your dream, and getting started; overcoming the fear of getting started living your dream life. (And most programs I see from dream gurus and coaches seem to be along these lines too.) Which is great for those who haven’t gotten started, but what about staying inspired once you’ve already STARTED working and living your dreams? What about staying inspired and motivated then, once you’re in the thick of the Long Slog that will make up The Rest of Your Life Living Your Dream?

It’d be great if the work itself served as inspiration, but let’s face it – there are days when that dream is anything but dreamy.

Where are the books and ebooks and programs that are geared to motivate and inspire when that dream is keeping you awake at night, but you don’t regret it one bit? That’s where I am right now; the daily grind of Living the Dream, the part that sure, you might hear people tell you about if you ask people who’ve done it, but it’s not the kind of stuff that sells books and programs, ya know?

Just curious why there isn’t more information about after happily ever after for entrepreneurs, and what your best advice might be for after the first few years. If that makes a bit of sense.

This is a great question. I also wonder where the resources are for people who are already ‘living the dream’. It’s unfortunate, but because there are no resources, people assume that if they’re having problems, they’re not really living the dream. So they get really confused and disappointed.

The second reason I suspect there are few resources available is that it’s hard. It’s very specific. People who want to quit their jobs? They’re low-hanging fruit, advice-wise. But a person who already has a lot of things right is harder. You have to really dig down to find the real problem. Plus, there’s way more variety in your average pool of dream-livers than there is in your average pool of cubicle dwellers. So it’s hard to find a big enough audience that a publisher is going to risk a book deal on it.

So you’re basically reduced to reading bloggers who know what they’re talking about and who want to handle the hard stuff. It’s all a numbers game, and in this case the numbers don’t add up in your favor.

But that’s all me ranting. Your question was, “What’s your best advice for after the first few years?”


Advice For The Business Owner Who’s Unsatisfied

There’s a few different things I might say, depending on your headspace.

If you feel like a failure because you’re living the dream but you’re still not satisfied, don’t worry. In the first place it’s not human nature to be satisfied, and in the second place, it’s a matter of tweaking your vision. When you were employed, all you could focus on was making a living on your on. Now that you’ve got your business, other things are going to come up that are going to seem like big problems. Maybe they are and maybe they aren’t, but likely they only seem like big problems because you already slayed the biggest problem in your life, and now with that out of the way, you’ll naturally focus on the next biggest problem.

An example. Let’s say you have a soul-sucking job. After much hard work, you jettison the soul-sucking job for a life of pie baking. But now the problem is you’re not making enough money. Pie making isn’t actually all that lucrative, and you’d like to retire someday. Don’t waste time feeling like a failure because your ‘dream job’ isn’t everything you hoped it would be. Merely view it as another challenge to solve. You could position your marketing differently so you could charge more for your pies. You could offer pie-making classes and ‘kits’. You could write a cookbook. You could start a line of adorable stationary and knickknacks designed to bring that ‘homemade feel’ to people’s everyday lives.

People assume that ‘living the dream’ is a destination. But it’s not. It’s an embarkation on a journey few are privileged to take.

Advice for the Business Owner Who’s Coasting or Getting Bored

But if, on the other hand, you’re finally leveling off after the grueling years of building your business, and you finally feel like you know what you’re doing and you have things under control, and you’re maybe even a little scared because things are too easy, I would instead ask you what your next challenge will be.

Because I think that if you’re the type of person who would challenge the status quo and have the perseverance to actually build a viable business, you’re the type of person who is not going to be able to sit still if things get too easy. So if your challenge is a little bit on the horizon still, I’d probably suggest that you spend 8 months or a year making your business really tight and lean and polished in terms of marketing and systems and how things work. If your challenge is within your business (like you’re breaking into a new market or you’re expanding your offerings) the healthier and more smoothly running your business, the easier those changes will be. And if your challenge will be outside your business, whether you’re running a marathon, taking a year to hike the Andes, or having a baby, a really tight business will be far less of a hassle for you.

Personally, that’s the space where I am in, and my attention is focussed on the mastery of my craft. I have a lot of functional experience starting and running businesses, but what do I really know? What counter-examples can I find to disprove my theories? How important is mindset? Philosophy? How do you know what’s a good idea, and when does it matter? How do you reckon risk, and is it possible that caution is a better bet than the standard mental model that entrepreneurs are risk-takers?

There’s tons of room to pursue mastery. I’ll be five years at it, before I’m even partly satisfied, and I think that would be true for most people. The learning curve of running a business is steep, and it’s intoxicating. But it’s kind of like mountain climbing. It’s easy to think, when you reach the summit, “Oh my god, I DID IT!” but actually, you’re only half-way there, and experienced climbers will tell you that the trip down takes a lot more skill than the trip up did.*


* That’s because you can’t grip as well walking down a slope, and momentum is all too often going to put you into a roll you can’t get out of. Plus, you’re already fatigued and thinking the worst is behind you. Prime recipe for disaster, right there.


You Already Know You’ve Got What It Takes. Challenge Takes On A Different Flavor Now.

Overall, people who’ve been in business for a few years are doing most things right– that’s the real-world definition of a successful business owner.

And because you’re doing so many things right, it no longer makes sense to do big overhauls. It’s too wasteful. You simply need to pick something that’s not quite up to par, and tweak it until it is. Whether that’s the amount of time spent with your family, or how you bid jobs, or how much time you *actually* get to spend on the parts of your business that you like, you’ve got the means to massage it into perfection. Or at least close enough for horseshoes.

But the trouble with tweaking is that it’s slow, and deliberate, and if you start tweaking too many things at once, it’s very overwhelming. That’s part of the reason I feel that reflection and oversight are so important— to give you that space to look for things to tweak, ponder how to do it, and record how it worked.

Like a shark, you get addicted to the challenge, the intoxication of being authentic to your journey, and you can’t stop moving or you die. That tends to mean risk– you’re probably not going to expand into sure-fire revenue streams (not least of which cause there aren’t any) so paying close attention to your inner compass is key. There’s nothing for you in well-tilled earth.