Growing a lifestyle business without losing the lifestyle

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Written By Nate Wright

15 thoughts on “Growing a lifestyle business without losing the lifestyle”

  1. Hear hear! I believe you nailed it when you said, “…your temperament, your appetite and the kind of lifestyle you want.” I’m finally coming to grips with this and choosing to stick with what suits me best rather than doing what others have found successful. We’re all different and that’s okay.

    Thanks for writing this.

  2. Great article for anyone, WordPress or no. It’s about buying back your time and whatever that is worth to you. Reading this and hearing you are clear as you are on what you want is inspiring, it’s what we should all be aiming for. Not the stars, just peace and acceptance in what we REALLY want.

  3. Wow, great timing, I literally just talked about this topic at PrestigeConf. Basically the synopsis of what I talked about was:

    – There are different definitions of success, and that’s ok
    – Different actions lead to different outcomes
    – Keep your actions pointed towards your desired outcome
    – Keep reassessing your desired outcome and adjust course as necessary

    The point being, most business advice is directed at the “grow/scale/get rich” crowd, which is totally valid for them, but would be the opposite advice someone like me would need to follow to stay small, agile, and keep having time to myself (for sleep, workouts, and experiencing life). And both paths, though completely different, are still valid reasons to be in business.

    Anyway, I love seeing other people talking about this 🙂

    • You’re absolutely right.I suppose small _and_ successful can sometimes feel like an anomaly, because the focus of the tech industry is overwhelmingly on big movers, VC-funding and hockey-stick growth (which, understandably, makes compelling news).

      But there are way more of us small players on the go, and we’re serving a huge market segment. We’re no anomaly!

  4. Over the last few years, I’ve worked hard to ensure that my business is driven almost entirely by choices that pushes me closer and closer to the lifestyle business that I want.

    I’ve been approached numerous times by potential investors and some deep pockets interested in acquihires of me and my team, and I’ve turned every one of them down. They could have easily made me a multi-millionaire by this point but that road has always been too far off the path that I want to trod. Do I have aspirations to be a multi-millionaire? Certainly, but only if the path that gets me there is inline with the lifestyle that I want.

    I genuinely believe that choosing to drive my business through lifestyle choices, not sacrifices, has put me and my team in a great place. Are there still struggles and aspects of our day to day work that we don’t love? Of course, but the end goal is always to move each one of us closer to a day-to-day lifestyle that we love.

    The decision to sell off some of my plugins recently was fueled by a lifestyle choice. I was tired of being stressed and over worked, even by the small amount that they added.

    The decision to begin limiting the 3rd party vendors we work with in Easy Digital Downloads was purely a lifestyle choice. If we didn’t love working with a vendor or didn’t thoroughly enjoy and approve of a plugin they built for our marketplace, why should we continue letting those relationships blacken our days?

    Each person that we choose to hire and bring onto the team is driven by a lifestyle choice. If that person is not someone I would enjoy spending a weekend with on a camping trip or someone I would hate to be stuck on an island with, they’re not going to be a good fit for my team. At times during the week, I spend more time interacting with my team than I do my family, so of course we need to get along well!

    Maybe I’ll trade in my king-of-the-hill cap and bring on partners. Not employees. Genuine partners with overlapping skill sets. Instead of being a go-it-aloner we can be two or three go-it-aloners going it alone together!

    Or maybe that’s just a terrible way to run a business.

    I personally think that’s a wonderful way to run a business.

    • Thanks for your reply, Pippin. It makes sense that, once you reach a certain scale, bringing on others can be just as much of a lifestyle choice.

      I suspect few of us will ever reach the kind of scale you’re working at. But I think one of the big lessons I’ve drawn from your posts about expanding your team is that the how and why behind a solopreneur’s expansion is just as important as whether or not it happens.

    • `Each person that we choose to hire and bring onto the team is driven by a lifestyle choice. If that person is not someone I would enjoy spending a weekend with on a camping trip or someone I would hate to be stuck on an island with, they’re not going to be a good fit for my team. At times during the week, I spend more time interacting with my team than I do my family, so of course we need to get along well!`

      Wise words 🙂

  5. Yesterday’s was probably the best curated Post Status Notes to date – I just read Megan Gray’s “Get Over Yourself” and this article back to back, and I can’t help but draw a parallel.

    I personally followed your path and tested many of the solutions you mull over above with mixed results. I fully agree that whatever the choice, like Pippin says, it should be driven by your personal goals and priorities as a human being. And testing partnerships, alliances, commissions, whatever is good – it’s not forever. If it works, score! If not, no biggie shake it off and move on.

    What I’d like to bring over from Megan’s article is how she mentions lucking into it. Now, I don’t think luck really had anything to do with it. I think her lifestyle, needs, priorities and ability to open the door on opportunities had everything to do with it. And I think that’s an important thing to keep in mind as we ponder how the ecosystem is evolving.

    It’s normal to ask and even to be a little afraid of how and where we might fit into things down the road. But I’d wager that those of us who are focusing on the work, have our priorities in line, are good people, remain attentive and are open to opportunity while being lucid about what we ultimately want…we’ll be just fine. We’re the kind of people who always land on our feet.

    • I read Megan’s post on your recommendation. Glad I did. I think she’s spot on. Perhaps because of my background, I’ve always had a reasonably healthy perspective on the tech world, and in particular what Theme of the Crop is (and is not) going to mean to me.

      It’s just a job, and one where I am privileged and economically secure enough to trade risk for flexibility.

      I think solopreneurs (or really the “entrepreneur industry” in general) fall victim to a lot of the same self-aggrandising narratives as the design community that Megan discusses in her article. We like to think of ourselves as exceptional, undertaking indispensable work, or taking on risks that others would balk at. We like to talk about how tough things are “on our own” and big up how hard we’re working (do you even #hustle?).

      I suspect if you peeled back the surface layer of a lot of entrepreneurs, there’s a less flattering mix of social privilege and character flaws that drive us out on our own. And I think you’re right that whatever it is that’s working for us, it will also help us land on our feet.

      I would call it confidence. My wife might call it “over-confidence”. 🙂

  6. Hmm… This feels like the first part of something. Lots of questions and pondering, but no actionable stuff. I do agree that having a lifestyle business is highly desirable for many of us, but I’m not sure of the point of this post – it just kind of fizzles out. So…. some thoughts on what this might imply:

    1) First, a definition. A lifestyle business needs to provide sustainable income. That is, it needs to let one live like an adult – in a decent residence, able to save some money, afford health insurance, able to actually pay for a vacation, etc. It’s not a side gig, something that supplements income while your partner really provides for the basics. The amount that takes will vary by person, location, etc but I think we all recognize when something is bringing in enough money to really support oneself (and any dependents).

    2) The traditional WordPress market is not going to do this for most people who are starting now. Any plugin category you care to name has at least one and likely several good premium plugins already established and likely a few good free options too. The theme market is likewise saturated. Yes, it’s possible there are small niches out there that aren’t covered but is it likely that they can provide, say, $75k/year for the next few years?*

    3) WordPress services might still be open. By services I mean hosting, support, etc. If one can get, say, $99/month for a combined hosting/support package it doesn’t take THAT many customers to reach my $75k/year figure ( about 65 or so). This risks becoming a business that needs staff, though (how do you go on a vacation when your hosted customers need support )? What do you do after you have enough customers to support you? Tell new customers to go away – or hire people to support them?

    4) It’s possible that the REST API opens up opportunities that previously didn’t exist. I’m working on one and I imagine there will be a lot of activity in this space as we all start to use WP as a way to store and manage content free from the post/page paradigm.

    * Before you say “But I can live well on a lot less than that per year!”, remember you will have overhead as a self-employed person that you don’t as a salaried employee. Healthcare for one – if your premiums are a modest $300/month, that’s $3600 in after tax expenses. In pre-tax money you may well have to make $5500-6000 just to cover those premiums. If you’re paying for a partner, kids, etc then that figure is almost certainly low.

  7. I love this post, and especially Michelle’s comment – is your talk videoed?

    I get fed up with “Startup” culture. Just this morning I was listening to Gimlet Media’s Startup podcast about a fast food company that took $2m in funding and ran itself into the ground because each product it sold made a loss. That’s not a business!!

    It’s SO refreshing to hear other people talking positively about alternative measures of success.

    More on my thoughts here: http://blog.wintle.me.uk/2016/04/on-startups/

  8. Fantastically great post. I’m involved with WP hosting on my end, and a lot of your points really resonated through with my own thoughts and feelings. Definitely some food for thought Nate, thanks for the write-up.

  9. Perhaps this post could be renamed ‘Why I’ve chosen not to grow my lifestyle business as I don’t want to lose the lifestyle’ – I was hoping for some more concrete tips on how to grow in ways that don’t compromise the lifestyle, not a brief overview of a couple of options which you have already rejected!

    My husband and I run UK WordPress agency Barn2 Media. We set up the company after quitting our day jobs and we want to be as successful as we realistically can be while still having the lifestyle we want. We have always been very clear that we don’t want to grow into a traditional company with a premises, staff etc. where we have to take on a minimum number of projects each month in order to break even – that’s not what it’s about.

    With this in mind, as the business grew and we started to attract more work than we had capacity to take on, we have tried various ways of scaling up without compromising too much. Some of these have worked for us and others haven’t.

    You are very dismissive of contractors in this article. There are many different ways to use contractors, some of which have worked for us and others haven’t. Over time, we have built a ‘virtual team’ of people who work together to develop WordPress websites and this works well, although we are constantly refining it. It allows us to scale up and down to meet the needs of each project, without having to worry about managing staff or ongoing salaries.

    It turns out that some types of contractor/skill are easier to manage than others. There are some skills that we haven’t successfully managed to contract out such as project management and the overall design of websites – whereas other skills such as SEO, implementing WordPress themes according to a clear plan, and custom WordPress themes, work really well within our virtual team.

    Another good tip is to increase your focus on ongoing services rather than one-off project work. A year ago, only 16% of our revenue came from ongoing services so we had to turn over a lot of new projects to keep up our income. Now, the figure is more like 45% as we have done a lot of work to improve and sell ongoing services to our existing clients. This allows the business to grow without compromising our lifestyle at all.

  10. This post strikes a chord with me.

    Prior to starting LearnDash I was on the road living in hotels every week working on consulting projects. After five years of this lifestyle I was getting burnt out. I loved my industry (e-learning and learning management systems) but hated being told where to go and for how long every-single-week. It also was putting stress on my personal relationships.

    It was while I was on the road that I decided to start a small blog (related to my field) that eventually evolved into our flagship product.

    For what it’s worth, our entire journey has been contractor driven. I have an affinity for contractors (probably because at one point I was one when doing consulting full-time).

    Finding and managing the right contractors is as challenging as finding employees. The benefit, however, is that ending contractor relationships is a helluva lot easier than firing someone. It’s more straight-forward and strictly business. Another important benefit when using contractors is that they afford you to be “quicker” (in many facets of your business).

    All that said, there is not a single “formula” for entrepreneurship. Contractors work for us because I have always understood that world and know how to maximize dollars spent. Partnerships, investors, full-time employees, and affiliates are all proven methods as well.

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