Doing It All

schmittastic fortune cookieThose of us bootstrapping for our business know what it’s like to be in charge of doing it all.

You’re the creative. You’re the design. You’re the employee. You’re the boss. You’re the accounting. You’re the maintenance guy. You’re the only one.

I sometimes worry what it would be like to have an employee in my future. As my business grows and I’m planning on a need for more help, I start to think and I don’t know if I’d be a good manager. Just because I started a business doesn’t mean I know how to properly manage a staff. From what I’ve learned with interns in the last couple years, I micro-manage way too much. Something I despised about my old boss. Who I left. To start a company. Oh Amy…

There are so many stressful things you have to go through as a small business, especially learning when to outsource. Analyzing whether something you need is something you can do yourself or if it would be money best spent on a specialist who can streamline the process. I absolutely advocate for giving the work you’re not familiar with to someone else, but on the other hand entrepreneurialism is making us quite the Jack of All Trades as they say.

I even outsourced something I knew I could do. Because I wanted someone to do it better. Funny thing is I’ve taught myself so well with other similar projects, it turned out I had to start the project over after paying for it and do it mostly myself. I just wasn’t satisfied with the original result.

And I’m not going to settle. Because I’m the creative. I’m the design. I’m the everything.

It’s all on me.

What’s your take on doing it all? Do you feel you’re depending more on outsourcing, a staff, or the self-taught process? Thoughts please…


  1. bradleymiller1

    I am definitely with you right now and trying to do everything myself. I am still in that “survival” mindset where I feel I need to be self-sufficient and maximize every available dollar. At some point though, and I have seen this in other companies, your thinking goes from “I need to do everything myself” to a growth mentality. You have that moment where you as an owner realize the true value of your time and that it is better spent on tasks that will directly make you money. That is where many of my clients are, and I would imagine many of your clients are there too – while they could do their own social media, they know their time is best spent elsewhere and so have brought in an expert to handle it for them.
    I guess the takeaway from all of this is that in order to grow our business, at some point we need to understand what we are best at and what we need to do to make the most money for our business, and delegate everything else. Now if I could just convince myself to hire an accountant to deal with my taxes…

    1. @bradleymiller1 OMG you definitely need to get an accountant. That’s not worth doing alone anymore lol. You’re so right about spending time on the money-making tasks. It’s what we all learn to do but we get so distracted with all the other things that need to happen that we don’t realize that we need the help to get us back on that focus. Thanks so much for the comment, Brad. Appreciate it as always!

      1. @schmittastic Very true, I do. Do you know any good ones you would recommend? I am always on the lookout for accountants and other professionals who deal with small businesses.

        1. @bradleymiller1 Sure. I work with Nathan at Basis Accounting. He specializes in small business and he’s a great guy to work with.

  2. edebont

    Interesting, I have seen similar behavior with project managers. The ones that do micromanagement want their team members to report every detail of what their doing and give the impression that they want to everything themselves. This will annoy the team members, spending time on the wrong things (reporting),  not getting the faith of doing their job well etc… which will in the end not produce a good result. 
    A good project manager will let his team members do their work. Have himself informed about the major issues, and manages them. In short a team-builder which has his team do the work for him in stead of doing everything himself. 
    Now, the above example is not the exact same situation you’re in, but I see some  similarities. 
    I think you should ask yourself these questions (keeping the above example in mind):
    – What happened that you had to redo the entire project mentioned in your article and couldn’t you have discovered the issue (of dissatisfaction) in an earlier stage ?
    – If I have an employee what do I want him/her to do ? Being I copy of myself so we can split the work, or do I let  hem/her do the things I am not good at or don’t like to do. It has to be clear what you expect from your employee to avoid frustration on both sides.
    – Am I an entrepreneur or a manager ? Am I capable of managing people so they can perform at there best or do I want to do everything myself.
    At the moment I think your are still are more entrepreneur (which is not a bad thing) than manager. But at least you are aware of your flaws (micromanagement) so I think you should be capable of growing into the manager role at a later stage if you want to.
    Thanks again for your article Amy. They are always a pleasure to read.

    1. @edebont Love your thoughts here. I definitely think management will end up being something I get help with. For now I think it’s all good with me going it alone, but that will change as things evolve a bit and I know exactly what I need to do to focus my time on what’s bringing in the money and therefore hire people to help me execute. Thanks as always, Erik!

  3. Wilde_Hunt

    I strongly relate to your article. I am a fashion entrepreneur and I literally do everything. It has gotten to the point where I have even had to learn photography basics to do my own product shots and purchase a professional makeup kit for when I work with models. I never had any intention of doing these parts of the business but I’ve found in most cases (with the exception of a few trusted professionals) I’m better off doing it myself. I’ve had photographers never show up to a shoot I spent months preparing for and I’ve even had photographers who never produced images from an 8hr shoot. The unprofessionalism I’ve seen is just crazy. I wonder if it ever gets better the more established you become or if it is always going to be this flakey…
    It’s really frustrating because all I want to do is create. I really prefer working with a team of professionals that all contribute their view point and skills. It’s like you said – “Jack of all trades” but the second part of that saying is “Master of none”. How can you master your primary occupation if you are also learning the careers of 10 other people?

    1. @Wilde_Hunt Absolutely. Sounds like we’re dealing with very similar speedbumps. How can we really get to a point of being an expert when we’re busy supplementing so many other areas. Unprofessional flakes are a big issue in creative I think. When someone loves what they do, they sometimes forget they have to execute when someone is paying them… even if it’s not their favorite project. They’re being depended on. Really good points in your comment, Larissa. Let’s try to steer clear of being the Masters of Nothing! 🙂 Looking forward to seeing you around more often. Thanks!

      1. Wilde_Hunt

        @schmittastic  My best friend (another entrepreneur) and I laugh about the extreme lengths we go to to accomplish the job. I try to look at it as good material for my biography. 😉  I think it comes down to the fact that not everyone is as passionate about their work and it’s hard to remember that fact when you personally would do whatever it takes to succeed. Thanks, Amy! Best wishes on your continued success!

    2. edebont

      @Wilde_Hunt The example you gave about the photographer not showing up is absolutely killing for business. I think in your case it is definitely worthwhile to put some effort in building a network of people/professionals who can assist you (and you can trust) in your business. This can be people from your schooldays or worked with in the past or a friend of friend etc..
      I am an ICT consulant (not an entrepreneur) working in ICT since 1995. During these years I have done many projects and actually backtracked almost all of my co-workers (the good ones) via LinkedIn. This gives a network of people and the opportunity that if I need a certain expertise I can track someone down pretty quickly.
      Now I know that LinkedIn is probably not a big thing in the fashion world, but that shouldn’t stop you from building a similar network  (LinkedIn is in this case is just a tool, an ordinary address book is also fine) of good professionals that will help you to develop your business. You really don’t have to do everything by yourself if you know good people.

      1. Wilde_Hunt

        @edebont Yeah, I have been doing this for 5 years so I do have a *very* small number of people I trust to collaborate with. Being in Columbus, there is a very small  pool of people working independently in the industry and even fewer of them have a decent work ethic and treat it like an actual job. 
        As far as networking is concerned, there are sites like Model Mayhem, which I do use to some degree. It is just so over populated with hobbyists that it  takes a massive amount of time to sort through the flakes. You may have a point, LinkedIn might actually be worth putting more time and effort towards. Lately I have been putting more energy towards establishing relationships with out of state stylists and bloggers with good results. My work is going to make it’s first TV appearance on the show Oddities soon. 🙂

  4. sdcrane

    My experience (personal and studying countless successful startups and companies) is that “going it alone” or “doing it all” ultimately is not the best way to Bootstrap.  Bootstrapping (what I did with my company from the very beginning, and now employs 75 people) is actually not doing it all yourself at all — it merely means that the funding for the business comes from CUSTOMERS rather than outside (equity investments or loans).  So even though I bootstrapped my business from Day 1, I never went it alone.  I initially started with a partner (so I never was alone) and then within about a year and a half we began hiring employees — and the bootstrapping continued because everything was funded by the customers / cashflow of the business.  I highly recommend finding and hiring great people.  There is no skill more important in business than finding good people to work on your team.  I think what social media consultants (and other consultants or marketing firms) struggle with is that they are not selling a product, but rather a service, and thus this boils down essentially to their “time”, which makes it more difficult to expand and hire in the early years.  The key is finding a set of clients/customers that pay the business on a recurring basis.  I prefer products that REQUIRE the purchase of the SERVICING of that product, rather than JUST a service (a la pure consulting or marketing services).  This is of course easier said than done because to create the product it takes funding and that can be difficult to generate from customers.  But to the extent that there are some products that can be created to offer your customers, and you can build/create them or get them created, and they can bring you recurring revenues, then the business not only has a much higher chance for success, it also offers the founder/owner (you) much more flexibility, opportunity, choices, and ways to grow the business.  And that brings me back to hiring.  When done wrong, it is a disaster (as you described with the task that you ended up re-doing, better), or hiring can be the very best thing a company can do — and usually is if done right.  While this may sound odd to new business entrepreneurs, but if you have the right product/service and the customers recognize this and are willing to pay for it and continue paying for it, EMPLOYEES ARE “FREE” — every dollar they cost you in payroll comes right back to you from the cusotmers — and then some.  And then A LOT some as you continue to build your business…

  5. SweatyBetties

    I am with you on this… I sometimes think “If I want something done right, I should do it” but then again, I couldn’t design my logo and graphics as good as someone else.. but I get cheap too… I always wonder how often I should be outsourcing and stop dicking around trying to figure things out on my own

    1. @SweatyBetties I figure if I can’t pull it off or make progress after a good day of trying, I’ve got to outsource it. You can’t afford to lost more time than that. And usually you can figure out early that you’re going to need help. There are always people out there that want to help, you just gotta remember you get what you pay for. Sites like make it easy to get graphics made cheap but they aren’t going to be what you’d have done with a paid designer on your side. One example. Thanks for the comment, as always!

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