Hey IHrs (Indie Hackers), what lessons have you learned after xx years of going/trying Solo?

I have been reflecting a lot lately on my IHrs journey over the past 20 years. I basically failed at all SAAS startup attempts - except for web agency work which I still do with some clients. Not being an Eng played a role for sure. 

Job/Work has almost always been painful for me. I blame myself for not finding one area I enjoyed and sticking with it. 

Regardless of all the failures, its been a fun ride. I would probably do it again - but with a more analytical approach.

What about you? What lessons have you learned?

Here are mine:

  1. Team > Solo. Try Solo if you wish, but quickly find a co-founder if you can
  2. Most Solo makers work on too-small ideas (related to above)
  3. If you are non-tech, its basically non-negotiable that you learn how to code. Not copy/paste. Really code. At least 6 months in Developer bootcamp somewhere.
  4. If f/t work is painful, building on the side is way harder. Fix work first.
  5. Desparation clouds judgement. Fix this so you can see "abundantly" and not short-sell yourself.
  6. Consulting/Agency isn't terrible, but decide if you really want it. Escaping this takes effort and friction (letting clients go).
  7. Build some serious mastery in a role before going Solo. Generalists don't do well in Solo - many Solo makers are masters in some niche.
  8. If you don't find your "role" in Job world early on, you will bounce between jobs and solo journey. It will suck more.
  9. FOMO clouds judgement. Fix this mental virus. Just cause some new tech shows up doesn't mean you should quit your day job.
  10. New Emerging Tech could be a great reason to quit and jump into the deep end. But jump in cause there is a business opportunity. Not because works sucks. 
  11. Work mostly sucks at lower-level startups. Thats why going FAANG is good if you can get in. FAANG has long runways so they can work on making work not suck.
  12. Many Solo makers try because work sucks. Its easer to get a new job, then build a Solo thing.
  13. Put 20% of Solo income into a "open when 50 years old" account. Don't touch it before then. I'm 51. I wish I did this.   
  14. Many Solo makers do it cause everyone is doing it. Social media is mostly positive stories (Feminine defies this though. They have smaller egos.) thus we don't see the "eating glass" part. I think many SMs (solo makers) haven't decided if they really want this life. 
  15. All lessons above you almost always learn by trying. My list is backwards looking and most Solo makers just starting won't believe me, even after reading this list. Ignore my list, try, and then make your own list when you are 50.

Been realising 4-6 and 12 the hard way in the last year.

Burned out at a job in 2022, haven't been able to give a damn about anyone's company since. And for me my peak output is heavily tied to how much I care. Still searching for something close to a job I can stick around in for a while for some stability, for now.

IHing is one potential solution I'm pursuing right now, albeit slowly with so much going on in life.

I like the way you phrased this: "peak output is heavily tied to how much I care". I think most founders don't get how important this is.

“Team > Solo. Try Solo if you wish, but quickly find a co-founder if you can“

Hiring in response to profit and building a team makes sense, but I’m negative on immediately trying to find a cofounder for reasons I described in another other post. This is a trade off where you’re adding risk and diluting your equity as some of the downsides. Whether or not that’s worth it is up to the individual and what kind of business is being built.

“ Most Solo makers work on too-small ideas (related to above)”

Define “too small” - if my living expenses are $1,000 but my idea produces $2,000 every month consistently, that’s a perfectly viable small business. “Small” ideas are only bad for venture capitalists who want an enormous return on their investment which is why they’ve brainwashed everyone to think that you must work on a Google sized business to be considered a success. I don’t live on their terms, and success for me is defined differently - the only thing that matters is that it’s not “too small” for me

Good points. Too small by my definition is too small for a given market need. eg: one dude making a mission critical app for Medical industry. I mean there are stories of one dev building an entire industry-changing app, but its an outlier. Thus why I say get a co-founder so you can remix ideas and make them better.

I appreciate your reply and will re-factor my list.

I wouldn’t even suggest you refactor - we don’t have to agree and maybe hiring a cofounder is what brings you happiness, in that case go for it. For my personal situation I’ve nixed the idea but we all have unique situations

Wait. Hold on. I re-read #2. I actually meant what you disagree with. Too small meaning the startup built is too small and should be bigger. So yes, I guess I do agree with "VC Bros" but not to make a startup investible, but stable and anti-fragile.

I've been freelancing since I was a homeless 17 year old who just wanted $20 to buy food to stop the gnawing pain. I was 6 when I sold card magic in exchange for lunch food so I didn't have to dig scraps out of the trash anymore, 7 when I started selling homemade bookmarks, 8 when I started flipping stuff at the flea market every weekend, and 10 when I started tutoring in math and sold a weekly book review publication (that's still on a yellow floppy somewhere in Florida lol). Mostly only school staff and public librarians bought it (probably to encourage me to keep reading and writing), but still, it was fun to make and sell. 😹

I definitely don't have a traditional story (I hope running away from home as a teenager to save their life isn't normal lol), and in many ways, I'm lucky I caught the entrepreneurial bug really early; I wish it had been under different circumstances.

Here are my top 10 tips I've learned in the last 15.5 years since I started freelance writing -- and have since evolved that into 4 separate businesses. (Though I focus heavily on 3 because the 4th is freelance editing, which is similar to my freelance writing business -- just a completely different audience.)

(And a bonus tip for funsies.)

✸ Tip 1: Don't be afraid to ask for the sale. It doesn't have to be this scary thing everyone makes it out to be, and you don't need to obsess about sales scripts. When I started, my (very literal) hunger overrode my anxiety about how I'd be perceived, and I walked into every business in downtown Tampa and asked if I could write an article for their blog for $20. Most said no, some said yes. The previous person's answer didn't deter me from asking the next.

Remember: Sales is a conversation between someone who needs/wants something (client/customer) and someone who is offering a way to meet that need/desire (you). The conversation is just centered on if you're offering something that makes sense to them -- from a solution and pricing standpoint.

That's it. I approach ALL sales calls from that conversational perspective and seek ONLY to understand them and their needs, not from the perspective of "I have to close this call." Put people first, and you'll win.

✸ Tip 2: Create systems early on. Your systems will be your best friend and how you keep from going off the rails when you scale or when life punches you in the face.

Everyone's systems & processes will be different based on what they're doing, but chances are, you'll have a few non-negotiables. If it weren't for my calendar, project manager + client portal (Basecamp), client onboarding process (Hello Bonsai + Google Forms), and outreach process, I'd be completely lost and wouldn't have the clients I have now.

Figure out what you need to operate your business smoothly (to increase brand awareness, to acquire clients/customers, to create products, to manage client/customers' expectations, etc), then continue to optimize your process. Your systems and processes should make your work EASIER, not add an extra burden on your plate. If you feel burdened (or if your clients/customers feel burdened), keep optimizing. Tip 11 will factor in this, but you'll see later. :)

✸ Tip 3: Don't skip branding. Not your color palette. font, and logo branding. I'm talking about your brand strategy. I'm a brand and content strategist, so I'm happy to go in more depth with this if anyone wants, but here are some non-negotiable things you absolutely NEED to have in place (or else):

brand values (what you believe in and how you operate your business), brand positioning, USP, differentiator, messaging, competitor analysis, client/customer avatars (not the bullshit avatars you find online that asks what their favorite beverage is, unless you're in the business of selling beverages), and voice.

Don't skimp on your brand origin story. I'm a FIRM believer 100% that if you nail your brand origin story (and tell the RIGHT story), you'll grow much faster and have a much loyal community base. (Loyalty is everything -- and this would be tip 12 if I had more space.)

Bonus if you know your brand archetype blend. (It makes creating content and visual branding MUCH easier.)

There's more, but this is a good start, and it's something you want to start working on in the beginning, while also recognizing that brand strategy constantly evolves. What you start with won't look exactly the same 10 years in because as you work with people, you'll gain more insight to tweak your message and stories.

A good next step: creating a stellar brand experience (and this is where systems come in).

✸ Tip 4: Don't "fake it til you make it." Be real and upfront with people about your journey.

If you're a newbie (or if you've pivoted to something new), own it! Don't pretend like you have decades of experience. Be honest with people if you have no actual client experience. (Trust me, people will still take a chance on you, AND they're going to be much more forgiving if they know you're a beginner and if you don't nail expectations.)

It's okay to be a beginner and suck. We all sucked when we started.

I've been a content writer since 2008, but I repositioned last year to specialize in writing for SaaS companies, a completely new-to-me audience. I'm not pretending to be an expert on SaaS content marketing, but I'm bringing in what I do know from my years of experience obsessing over content marketing and sharing my insights in the SaaS industry as I learn along the way.

Raw honesty is REFRESHING and will absolutely set you apart (in a good way).

✸ Tip 5: Entrepreneurship means you're committing to a lifetime of learning. You never "arrive" or know enough to stop learning. The landscape of entrepreneurship constantly evolves, as does whatever industry you choose.

(As a marketer, it would be laughable if I said I know enough to not stay on top of current content marketing trends. I'd be obsolete in a few months, if that lol.)

Stay open and keep learning. The ones who pretend they know everything and think they're better than everyone else are the ones who don't last.

Also learn about stuff you're NOT claiming to be an expert in. When I was writing articles, I learned about email marketing, even though that wasn't my area of expertise. Doing this allowed me to start offering it as a bonus service to current clients.

I also have 5 degrees in different fields, which means I bring in my knowledge of psychology and cultural anthropology to my work, allowing me to further differentiate myself and my framework.

The core principle: Don't limit yourself when you learn. Learn for the joy of learning.

✸ Tip 6: Center sustainability in everything you do. This means in your business (having sustainable business practices to ensure you meet your goals and deliver a quality experience) and in your personal life.

I'm someone who deeply struggles with mental health, has a chronic illness, and is a single mom of two kids. I'm also recovering from burnout from when I WASN'T centering sustainability.

(I burned out for 2.5 years to where I was incapable of doing the bare minimum in my business. It devastated me financially and mentally. Don't be like me.)

Recognizing there are seasons in our life and choosing to honor those seasons and work WITH them instead of against them will benefit you a lot. Yes, it takes work and effort to build something real, BUT you should not be grinding out 22-hour days to do it. You will burn out eventually, and all that effort will go in the trash.

Build something that'll last, and that requires future-oriented thinking. (And systems. You can't escape them lol.)

✸ Tip 7: Build a BRAND, not a PRODUCT. This includes tip 3, but it goes deeper. When we build a brand, we're building something bigger than just us (even if we're a solo operator). We're building something people can rally behind. We're creating something behind an IDEA, and ideas can't be destroyed as easily as a product/offer.

Products can be duplicated easily, and we see this ALL THE TIME. If someone creates a product, it's not long before someone tries to create a better one or a cheaper one.

A big piece of this is community. If you focus on growing a community -- not just an audience -- you'll set yourself up for success a lot faster (and way more sustainable.

Here's my distinction between audience and community:

Audience: communication/interaction flows one way -- from you to them OR from them to you

Community: communication/interaction flows ALL ways -- from you them, them to you, and them to each other.

Essentially, it decentralizes leadership so you aren't the only one who has to produce to sustain your business. Decentralize as much as possible (including if you have a team backing you up).

Brands (especially one with community in the center) can't be stolen or duplicated, even if someone steals/copies your framework, content, and product/offer.

✸ Tip 8: Figure out very early on if you are a visionary, operator, or both -- then act accordingly.

I won't get into all the differences between visionaries and operators (look it up on Google), but this is CRITICAL to your future success.

If you are a visionary and like coming up with ideas but have shitty follow-through, get a co-founder/get a #2 who is an operator so they can execute your ideas.

If you are an operator and like to be in the trenches creating and delivering but aren't great at generating lots of ideas, get a co-founder/get a #2 who is a visionary.

If you're like me and are a unicorn (both), you can go solo if you want, but you can also hire a team/get a co-founder.

The principle here is simply: Play to your strengths and outsource your weaknesses.

Doing anything else means you're acting out of ego and won't last very long. You need BOTH a visionary AND an operator to succeed, and it's okay if you aren't naturally both.

Remind yourself what's important: staying in business.

✸ Tip 9: Define where you're going and how you're getting there -- and protect that plan ruthlessly.

If you don't plan where you're going, the world will tell you for you (and you're going to be unhappy and frazzled). The first thing I do with all my clients is set up OKRs with them. That's objectives + key results for the year and current quarter. This gives us a VERY clear roadmap of where we're going and how we're planning on getting there.

That way when shiny objects pop up (and they will), it's very easy to discern whether it's a distraction or a useful opportunity because it's clear if it aligns with our strategic plan.

Now whether or not the roadmap we create ACTUALLY gets them to where they want to go is a completely different conversation for after the quarter when we assess and revise as needed, but the important part is COMMITTING to a path.

I use a tool called WeekDone to track all this for me and my clients, and I 100% recommend them. I'm a solo creator, so I set up my account by business (Scale With Words - content writing for SaaS businesses; Startups With Soul - strategy and DFY services for solo creators; Brandcrafters Guild - membership community + digital products for solo creators). I break these down into "departments," as if I have a team (even though it's just me), so I have admin, marketing, sales, and customer service departments for each to make sure I'm improving each of these areas for each of my businesses.

I've been setting up OKRs for clients for years, and I'd be happy to run a workshop for WIP members to do the same if people are interested.

It should be FUN creating OKRs, and if it's not, you're probably not a visionary (and you should re-read tip 8).

✸ Tip 10: Surround yourself with people who normalize the lifestyle you're working for. It was one of the hardest things I had to do when I stopped hanging out with people who were content being average and living the life society plans for us (working an unfulfilling job and living to party on the weekend or delaying joy til retirement).

This isn't to say cut everyone out of your life and go completely monk mode. That's ridiculous. You can still have friends who work a 9-5, but they should have SOME kind of goal or direction in their life. Goal-oriented people keep you goal oriented.

You DO NOT have to pay tens of thousands to be involved in a mastermind (and most of these are created around the idea of "you become successful by being in someone's energy" [not true] and it's no more than an expensive circle jerk to fund a guru's lavish lifestyle to get them more clients by flaunting that lifestyle [ahem Tai Lopez and Dan Lok]), but you DO need to be in community with people who have similar core beliefs as you and who are either working toward the lifestyle you want or who are already living it.

WIP is a good community for this, but you can belong to other communities where the conversation is multi-directional and there's sharing of knowledge/experience.

If you can't find a community you'd want to join, then create it yourself. This is a part of tip 7 -- build community. It's the #1 reason why I created my own free community (Wild Creatives) and paid membership within that community (Brandcrafters Guild). The conversations there are different than in other communities I've joined because I, as the founder, get to set the tone. And there are no circle jerks lol.

✸ Tip 11: Stop replying on assumptions and instead always ask for feedback -- from your audience, community, clients, customers, fellow creators, etc.

I continually ask for feedback during multiple stages of a client project (and it's all automated with the systems I've put in place). I put a premium on client/customer experience, which means I'm constantly gathering feedback to make sure I'm delivering the best experience as I can during every touchpoint someone has with me and my brand.

Entrepreneurship is a continual learning process, and I've confronted very uncomfortable truths about who I am as a person then did the even more uncomfortable work to become a better person/provider.

(For example, to get vulnerable, I have an anxious-avoidant attachment style, so when I get really anxious about a client's project -- like if I'm about to miss a deadline and need an extension -- instead of communicating that to the client, I would go radio silent and just drop off the planet, even when they'd message me. It's because I was trying to avoid looking like a bad service provider by asking for an extension, but the reality was I was leaving them in the dark and making THEM anxious by ghosting. I placed more value on the quality of work I was doing over ensuring the client had a good experience overall, and I paid the price for it many times when I lost long-term contracts. Realizing this about myself allowed me to create a system to make communication easier and less anxiety-inducing for me + a way to update clients on their projects regularly instead of just at deadline time, so we can adjust the deadline as needed BEFORE it got out of hand.)

Also, collecting feedback on digital products allows us to make them even better.

I frequently run paid workshops, and the most common piece of feedback I got was it's too long. (Like I'm holding people hostage for 6 hours too long lol.) So instead of trying to cram 5 days' worth of info in a one-day workshop, I break down the scope covered so it's much more manageable and people are able to buy additional workshops that cover the rest if they choose.

My concern (and assumption) was that people would rather buy ONE workshop with everything in it and wouldn't want to buy multiple workshops, but I was completely wrong.

Asking for feedback continuously allows you to not rely on assumptions and instead create and refine using data and facts.

❤️‍🔥 I'm curious: Which of these tips did you find the most value in? ❤️‍🔥

I'll take the one that gets the most votes and write a Substack issue next week that goes into it in more detail while showing how I implement it in my own business and how you can implement it in yours.

(PS This is tip 11 in action 😉)

Thanks for this! A lot of golden tips.

The fact you read through all that 😭

Of course! Your insights here were so valuable. Truly appreciate the effort you put into sharing your expertise!