Stop aiming for the trees
Kyle Racki

On Patience and Self Confidence

Note: I apologize in advance for the length of this reply, given that the recommended length for full stories is 7 min… sorry!

Thanks for sharing this experience, Kyle. So many thoughts! None of what follows is meant to be critical, I’m just looking to pick your brain a bit more if that’s cool.

To start, here are my thoughts on each of the points you outlined about Katie:

Since her children are small and her husband runs his own busy medical practice she only has time to work on her business after her children go to bed.

I don’t really see anything wrong with this, as a first impression. Everyone has constraints they need to work around, the need to balance risk and consider other responsibilities. Basecamp was built with only 10 hrs a week while they ran their Agency, and — while I don’t know many details about Proposify (just what was written in the Groove blog and a couple other articles) — didn’t you essentially do the same thing? If Katie wants to build a business, then, depending on the details of her circumstance, maybe this is the best way — an hour or two a day. Little by little, a little becomes a lot.

Everyone’s situation is different and I think the key is just finding a way to make it work. I was somewhat thrown into freelancing. I had been working in an entry-level position at a small accounting firm for about a year while still in school (for accounting) when the firm decided to restructure their services a bit and focus less on small business bookkeeping and more on corporate filings. That meant my position was going away, so, the CPA there offered to refer to me a couple of the clients whose bookkeeping I did, as it was work the firm did not intend on continuing. From those couple clients, working part-time, I grew my freelance practice to the point where it started to compete with university and had to take a semester off a couple times. My freelance practice later imploded for a variety of reasons (read: mistakes), but that’s another story.

I can’t entirely remember now what my feelings were towards freelancing at the time if I was planning to already and just got thrust into it early or not, though I do remember feeling restless in the traditional office environment. But I digress. The reason I shared this story was to say that I think that was actually a pretty good way to start up freelancing. Luckily I was still living at home, so expenses were low, but imagine applying that scenario to where school is instead a day job and pretend it was entirely my decision to start taking on clients on the side. Then build it up to the point where one can quit the day-job and presto — like your story! I consider this a much better option to just dropping everything and jumping in cold with both feet. Unless you have some savings as a cushion, but even still. It’s inevitable that the freelancing business will grow one client at a time, so why not just do it in the evenings until it’s really starting to compete with the day-job before making the jump?

She used to manage people’s social media for them but isn’t taking that on right now because it doesn’t pay enough and it isn’t scalable.

Here I think my instincts are pretty much in line with your advice. This seems like a perfect example of “imposter syndrome”, when you feel like you’re not good enough to charge the big bucks but the service isn’t sustainable at the low price. But instead of raising prices or going after bigger clients you stop the service with the conclusion it’s not feasible, because it’s true it’s not feasible at the low price and you don’t think you can charge the high price. The theory that a certain service is just not scalable is easy to disprove when there is indeed a large company you can point to doing exactly that at scale, such as Vayner Media. The key here is to find a way to overcome the imposter syndrome and charge more, target different clients.

I am all too well acquainted with this imposter syndrome (aka self-confidence issues). I had it all during my freelance accounting. I have it now with my desire to write, and with the invoicing app I’m building. I’ve also heard it repeated many times from founders who have overcome it, they insist SaaS companies routinely don’t charge enough — the large majority are undervaluing themselves. So it’s clear we’re not alone in this.

For a number of years (summers mostly), a friend and I ran a mobile car wash and detailing service. We struggled a lot with pricing. We thought we had to be the same price as the local “fixed” carwash, and when we raised the price a bit (out of necessity) we found that we were then just getting the people with absurdly dirty cars treating themselves to a hassle-free cleaning that took two hours to do and more than defeated the point of raising prices. We invested in a truck and built-in equipment to try and trim as much time off of each job as we drove around town washing one car here, there and everywhere. After much trial and error, we finally found our market. Not commercial washes (tried that), not dealerships (tried that), not company lots (tried that), but condos — or, rather, luxury condos. It was a long and bumpy road, and we essentially got there by just continually raising prices and seeing who was left. We were charging twice as much as when we started and this demographic would happily pay it. What’s more, condos are places where we could wash for many customers at once and drastically cut down on travel time, not to mention also operate year-round (indoor garages!).

The problem was that we were never charging for value. We struggled hard with imposter syndrome and pricing. We had a hard time believing we were worth that higher price. I totally take your point about how much better it is to be big and how hard it is to stay small. While we were of course still a tiny operation, I feel like it still applies. It would have been miserable to stay the small operation with our truck, driving around doing single washes, barely making things work. This change positioned us to at least possibly be able to grow bigger; armed with higher prices and a new model. It was immediately more enjoyable. We could provide better service and see a path towards growth and profitability. I imagined making it like the 1–800-Got-Junk? of mobile carwashing (so impressed with what Brian Scudamore has built). Unfortunately, this only happened as we both were already moving on to other things. Probably some lessons here on quitting/committing, or maybe it’s the same old imposter syndrome at work. I had just lost confidence over time that we could grow it to be a big successful business.

She charges $500-$1,000 for websites but is working up to charging $5,000.

I think my reaction to this is same as my thoughts on the previous point. Charging small at the very beginning is fine, I think. Everyone’s got to get started and get off the ground. I did that with my freelancing. However, I think you should move away from those rock bottom prices as quickly as possible. As soon as you have one or two examples to point to, start charging what you’re worth. Charge more than what you’re worth — why not? See what happens.

She is going to work on the business more when her children eventually start school and hopes to one day have a team of people running the business.

Here too I think my thoughts on this have already been expressed, under the first point responded to. The only thing I would underline here is to not postpone the whole idea to a time “someday when the kids are in school”. I know all about procrastination. My reasons are different but some examples can map back on to this situation well. There’s a time in the future when you think things will be perfect to allow you to do X, but the truth is there is never a perfect time. I think that’s true for everyone. When that supposed perfect time finally gets here, there’s something else preventing you from doing X. And all the while you may be telling yourself you’re working on X, but the truth is you’re actually holding off from doing the real work because you’re waiting for that perfect time. Then, next thing you know, it’s much later — later than that perfect time even — and nothing’s been done. The key is to just slowly and consistently do the work. Bit by bit and you’d be surprised what you can accomplish over time. I feel like I’ve possibly responded to something that was not even said, so perhaps I just wanted to share this bit about procrastination because I struggle with it.

Also, I am not a parent and I do not mean to come across as equating raising kids to just procrastinating starting a business. I’m simply trying to share my belief in the power of small consistent steps and evenings. I absolutely recognize the amount of time kids require, which is why I’m comparing it to a full-time job. And just like in the scenario of building a freelance business, I see nothing wrong with first just working during your down time. Then, as things grow, you could make certain decisions and trade-offs for more time such as daycare, a weekly nanny day, or something along those lines — I wouldn’t know.

A few comments on some of the thoughts you shared:

Case in point, Gary Vee started his agency the same year I started mine (2009). His now does $150M in revenue and has 800 employees. Mine never hit $1M and was sold for parts in 2014.
What’s the difference between us? Gary Vee doesn’t just aim for the stars in our galaxy, he aims for the super clusters. I aimed for the trees.

This makes me think of one of my all-time favorite quotes: don’t compare your beginning to someone else’s middle. I like your comparison, it’s very powerful, but I feel that it’s not exactly fair. While you both started the same type of business in the same year, and it’s obviously true two people can achieve completely different outcomes as the result of a small difference (thinking bigger, for example), I think you were just each at totally different points along your respective paths and coincidentally happened to start an agency at the same time.

From the sound of his story at the beginning of The Thank You Economy, it seems like Gary had been working in his father’s store since a young age. Then in 1999, after graduating college, he took over running the company and continued to do so until 2011; growing the business massively in the process. In 2006 he started Wine Library TV on YouTube which (I think) is about when he decided to get involved in social media in general, start giving talks/presentations and overall build his personal brand. He started his agency in 2009 but only started focusing on it full time in 2011. Looking at this series of events you can notice some key things. First, he was probably incubated in a business environment almost his entire youth. When he took over running the company he honed his skills for a solid 7 years, from ’99 to ’06, before spreading his wings. Then he slowly built new skills and a strong personal brand for 5 years before committing fully to a new business, Vayner Media. His work ethic is also practically inhuman (check out his DailyVee series on YouTube), so people also need to decide if that’s for them.

I feel like there’s a significant age difference between you and Gary too, but I’m not a fan of using age as the benchmark. Rather, I’ll just extrapolate my idea of the path I see you on. I know things are entirely different on the inside than when viewed from the outside, especially with the gloss I’m about to apply, but from what I know about you, it seems you’ve been continually moving into bigger and better things as if in a Tarzan-swinging motion. From job to building a freelance practice, to building an agency, to building a successful product company, to now — where I see you focusing more on writing and sharing. Maybe a few years from now you’ll have a very successful software company and be a “big name”. Then, say at that point you start a new business and it goes from zero to awesome in just a few years. Even if that’s not an agency, I feel it would be a more fair comparison to Gary today (not Gary in future) than the one you made comparing like with like (agencies).

A few hours per day during the week just isn’t enough time to build a business. Not in the early days. No matter how productive you are, you need to maximize every hour in the day. Don’t wait years to work on your dream. Your children will understand.

I absolutely agree with the last part here, “don’t wait years…”, as was essentially echoed in one of my responses above. However, I think starting with a few hours a day (or even just a couple!) is a great way to start — as I argued above. You seemed to have done the “few hours a day” to build your freelance business while working a day job, do you regret that? What do you think you should have done differently? I’d love to get your thoughts here.

If building a business is important to you, tell your partner. He should be able to understand, especially since he’s also self employed, and support you in assisting with childcare. In a relationship, neither partner’s dream is more important than the others.

I absolutely agree again, that neither partner’s dream should be more important than the other’s. I’ll stress here again that I don’t have kids. I am married but we’ve decided that having kids is not something we’re ready for or interested in yet. With that said, I assume that when people have kids it is something they both wanted. Kids are a big responsibility and require time; I have to assume future parents know this heading into the endeavor so I don’t really look at it as some kind of imposition or burden when they must have decided it was a worthy project to pursue. With that settled, now there are two things that would need doing: the family needs to be cared for and provided for. Simple division of labor. How couples choose to do this is entirely up to them. In Katie’s position, it seems like it might actually be possible for her spouse to control their schedule and maybe exchange a couple days of work for childcare so that she can work on her business. However, I feel like a more common scenario would be a full-time job where the time commitment is not exactly negotiable. If that were Katie’s position that would makes things a bit trickier, would it not? This is where balancing risk and current commitments comes in, and everyone’s situation is different. If they make enough money to pay for childcare to free up some time, perhaps that’s an option. Or as I argued above, since a business grows slowly no matter whay, why not work at it in the evenings until it demands more? Treat both spouses’ commitments as jobs, and trade roles when her partner gets home so her evening starts as early as possible to work on her business. On the other extreme would be her partner quiting their job to take over child care, and her working full time on the new business, but this doesn’t strike me as the most responsible thing to do. For me, that would be a little too risk-heavy.

If the business you’re currently working on isn’t your real passion — quit it, skip the line and work on what you’re passionate about now. Having a breadwinner who can provide a soft place to land is a massive opportunity for you to go out and try things without fear.

I’m very curious what this other type of business is, where Katie’s true passion lies. How unrelated to web design is it? If it’s as unrelated as landscaping, then yeah, maybe shift focus now and stop wasting time on something you know you don’t want to work on — especially if the income is not absolutely needed, like if your partner can support you both (not true if single or single-parent). But if the future business is at all related or you need to make an income as you build your dream business, then I’m 100% for the Tarzan-swing approach like what you and Basecamp did. Do you wish you did things differently?

Thinking big to me means two things: being patient (thinking long term), and having self-confidence — believing in yourself. Things take time. I almost wrote “sometimes things take time”, but I don’t believe that true. Everything takes time, and sometimes maybe you’ve got to build your dream business in steps. I think that probably happens regardless, just maybe the steps are more clearly defined for some — like if Katie were to build this first business as a launchpad to her dream business.

I think the co-founder of BigCommerce, Mitchell Harper, wrote a great article on that topic here:

One last question, what do you mean when you say “I aimed for the trees”? What does aiming for the trees look like versus the stars? What did you do or not do that could have been different, or that you wished was different?

Lastly, your article made me think about an article from Joel Gascoigne that is somewhat about not thinking big. I thought it might be interesting to share, so here you go.

I’ve realized over time that two pretty much exactly opposite things can both be true, and I find that very interesting. I think what makes the difference is the time or circumstances and the type of person you are — what you may need to hear. For example, the old adage “if it’s worth doing, it’s worth doing well”. I could not agree more with that statement, right down to my bones, and that’s sometimes the source of my problem I feel; I’m worried I can’t make it perfect so I procrastinate. Then I heard something Gretchen Rubin said on the James Altucher Podcast along the lines of “do it slowly, do it badly, do it ugly, but do it”, and that rings just as true to me. It speaks to the power of action over ideas, to small steps, to consistency. It essentially directly contradicts the first quote but they’re both true for me. I need the latter one to get me going, and then once I’m doing I can’t help but want to make whatever it is I’m doing the best I possibly can.

This is what intrigues me most about where I perceive myself disagreeing with you, maybe there’s something more to know.

Thanks again Kyle, keep sharing.