Advice for People ‘Living the Dream’

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  9. “I need to charge more. Is this a valid reason to raise my prices?”
  10. Q&A: The Fundamentals of Growing Your List
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  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.

[Tweet “People assume that ‘living the dream’ is a destination. But it’s not.”]

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.


16 thoughts on “Advice for People ‘Living the Dream’”

  1. This is a perfect question. How to maintain motivation and inspiration in the daily grind?
    From what I’ve read motivation comes from feeling like you are connecting to a higher purpose,  making progress, and connecting to a group with shared goals. Focusing on the skills to do that seem to create intrinsic self-perpetuating motivation. Personally, since I work alone a lot, I focus on the first two.
    I craft my daily goals to align with my dream and focus on making progress. Here are a few questions that help: Does doing this task move me toward my dream? Am I learning a valuable skill? Am I building my energy source (money and skills)? Do I touch my dream in some way while I do it; in other words, is there some way I can shift my daily task so it includes some aspect of the life I want to be living in my dream? And finally, what is the fastest thing I can do to end up with something to show progress?
    Then there is the practice of Flow, tuning each task so it’s challenging enough to be almost frustrating. Even with menial tasks it helps to make them challenging. According to Mihaly Csikszentmihaly, who wrote the books on Flow, boredom comes when we aren’t challenged enough.

    1. @PilotFire I too, find that making sure the daily goals tie in with the big picture goals is the only way to make it happen. I like your point about making the mundane challenging; part of why I so like to systematize is because there’s a challenge in executing perfectly.

  2. I would sooo not sit still if things started to feel easy in my business. But I would sooo love to have the feeling that things we’re getting too easy sometime soon.
    Great stuff, Shanna. And great question, Abby! There really should be more people in the “what happens after happily ever after” space. But you’re spot on in that this “I’ve already quit my soul-sucking job and have been slogging away for years” market – if you can even call it that – isn’t low hanging fruit. This territory is constantly choppy water with a hurricane always threatening to blow in.
    For now, I’m trying to figure out how to communicate what my business is all about and why it’s valuable to such a diverse community. Some systems are tight, many experiments are in process, but the marketing… oh, the marketing. Man, I gotta step the marketing game up big-time. It’s my biggest business challenge and I imagine will always be. Even one day, when I’m “successful,” things are clicking, and the sun is shining, marketing’s still going to be the bane of my business existence. But it’s good training for marketing myself – to my wife, my local community, and other important people – and learning how to effectively sell. In many ways, becoming an entrepreneur teaches you the skills that we all should have in our personal lives. It just takes a looong time.

    1. @joeyjoejoe I had an insight about marketing this morning. I’ve been researching MVNOs, basically resellers of broadband to port my Sprint phone to because they’re usually much cheaper. Wikipedia has an article listing all the MVNOs in the US. So went through the list and opened all the websites. Some were terrible– If I hadn’t known what I was looking at, I don’t know that I would have figured it out. Others were fine, but they wouldn’t let you bring your own phone– you had to buy one of theirs. Others were a bit opaque on their pricing structure. 
      But one of them, Ting, offered “16 reasons to use Ting.” The had an interactive chart showing you exactly how much money you would save. They allowed you the option of bringing your own phone, buying a new one, or even buying a refurbished one. The directed you to third party sites to show you want the coverage would be like in your area.
      On it’s own, the site is excellent. But compared to the others, the site is OUT-FUCKING-STANDING. It pulled out all the stops to show me why the service might (might!) be right for me, explaining honestly about it’s constraints and what it can and can’t do (and why!). 
      Ting is selling exactly the same thing as at least a dozen other services, but they’re selling it better, because they’ve taken an interest in finding out exactly what you need to know in order to be compelled by their service, and they do it in a totally open and transparent manner.

  3. I’m not to the point yet where most of this applies to me — I’m still working on getting this business up and running. But in terms of maintaining motivation and inspiration, the best tool I’ve found is my own writing. Nothing inspires me to refocus and get to work like reading my 5-year vision from Your Next 6 Months (Forever). I also keep articles and newsletters I find resonate well to read when I need them. (Like I should probably keep this one for when I’m out of the “Ooh! New(ish) business!” phase and getting into the daily grind bit…should I be so lucky as to get there…)

  4. I agree with David on this. I get bored quickly without a challenge and boredom for too long leads to me staying unmotivated and having a hard time getting out of that rut. I think if I was at a loss on how to challenge myself, I would just check out what other people in my field was up to. Sometimes seeing someone else work on something challenging will inspire me to do the same and I’ll try to stretch myself more.

  5. michaelwroberts

    My challenge is sort of on the opposite end of the spectrum. I can get so wrapped up in finding motivation that I lose the discipline to keep getting things done. I tend to rely on bursts of motivation to get things done instead of just plowing through the challenges at hand.
    That said, community is a major boost in keeping me going. Getting the chance to chat with others in the same space provides me with new insight and energy.

      1. michaelwroberts

        @Shanna Mann   Because I’m in the SEO / online marketing space, I find that Google+ is helpful. Lots of people within that community lose that network. I also get a kick out of quick interactions on Twitter.

  6. It looks simply smashing over here, Shanna!  Tried to subscribe again.  Let us see if it takes;)  My habits feed the results which in turn feed the habits.  So it easy now to say, yeah CJ, you’re tired, don’t be a wuss, do you want to fit in your pants or not?  And I do the freakin’ plank whether I am overjoyed about it or not. Then as you say the reflecting part comes in where all the tweaking is made.  It has become game around here and it is fun, fun, fun.  
     @joeyjoejoe Yeah man.  I am with you. Ya gotta learn to sit with the easy sometimes.  Constant challenge which inevitably comes with working at our frustration level all the time is simply too exhausting to keep up indefinitely.

  7. Hi Shanna, I am loving the look of your site, Shanna.   Total class.  
    I like the point you make about there not being much out there on people already living the dream or the Hey, I’m Kinda Living the Dream crowd.  I rely on blogs for the most part as I’ve not seen a book out there that deals with it.  Our tutoring/guitar business is going smoothly.  Although it does take some hours, we both have a handle on what needs to get done for students to learn and people to spread the word.  Our novelty has been in starting the blog.  That has been a huge learning curve, and the fun and exhaustion that comes out of writing a book and promoting it is keeping us focused a bit these days.  The challenge is in the tweaking of exercise and scheduling to make sure we continue to make time for daily fun.

    1. @tammyrenzi Sounds like you have things well in hand (and there’s no money to be made off of you ;)). What’s next after the blog? Or does that challenge still have a lot of life left in it?

      1. @Shanna Mann I think we are about ten years behind, so we have plenty of work to do.  As for making money off us…how about we get people off the hamster wheel and send them to you!  Come to think of it, we should have put that at the end of the book.  
        New Conclusion:  when you do finally leave your hellish nightmare of a job, please see Shanna, Joel, Erin, Sarah, et al.  🙂

        1. @tammyrenzi 10 years behind who? It’s true, the market of people who need advanced or even intermediate advice is miniscule, compared to the beginner market. It’s a shame so few bother with it, but then, when you get that far you’re pretty self-sufficient by that point anyway.

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