The Solopreneur’s Dissociative Identity Disorder

When you start a new business, one of your goals is to “be your own boss”.

Usually you start with a very small team or no team at all.. you are all by yourself. Yes! you made it! you are “your own boss”, but you are also “your own employee”, “your own investor”, “your own accountant”, “your own sales team”, “your own janitor”,… your are a Solopreneur (solo-entrepreneur).

Meet the parallel personas that live in a solopreneur’s mind

There are at least three distinct players (or groups of players) that come together to start and run a business: Capital, Management and Labor.

• Capital: The Investors. They provide the resources (money) required to start the business. Their main goal is to maximize the return of their investment (make more money than what they put in). On small businesses and startups, investors are usually very involved on the early stages, leading the big picture and strategic decisions and as the business grows they get disconnected from the day to day and delegate most of that to managers.
• Management: Is an agent of the investors and looks out for their interests. Takes the resources that the investors have put in place and organizes them in a way that generates a product or service of value, which can generate revenue and eventually profits.
• Labor: The workers or employees that produce the actual output of the business. At a very simple level, the workers trade their time/talent/focus/effort in exchange for a salary or an hourly fee.

When you are a solopreneur, you play all three roles at once. You shift from one to the other multiple times during the day.

Avoid being permanently stuck by compartmentalizing your mind

To be successful as a solopreneur, you need to be aware of these roles and shift from one to the other as needed, without stopping progress. Once you are done with one role, you need to get back to the other making a complete shift of mindset so you can focus on the task at hand without getting distracted by thinking about the other roles… if not will fall into a state of “analysis paralysis”:

“the state of over-analyzing (or over-thinking) a situation so that a decision or action is never taken, in effect paralyzing the outcome”

To illustrate this problem and how it usually happens, here is an example: Imagine you just got a brilliant new idea that sparked your entrepreneurial spirit and you just quit your job to pursue it. Here you are thinking as an investor (capital), taking a risk. You take all of your savings and time to work on the idea, how it will be developed into a product or service, plan steps to get to a prototype, launch, how your first year of operation looks like, etc…

Now you shift to the manager role, with the mission of executing the plan in a way that eventually accomplishes the long term goals of the investor. As you work on “manager mode” you define action plans for all the steps needed to hit the goals set by the investor, you break those goals down to step by step action plans that then start sparking the need of labor… meaning, specific blocks of productive work that need to be completed by an employee. Depending on the nature of your business, these are things like “design a logo”, “create full product specifications document”, “create full UX map of app”, “design screens (UI) of app”, “rent office space and furnish it”, “keep accounting books up to date”, “develop contracts/legal paperwork”, etc.

How and when do you get stuck?

The analysis paralysis state comes when you are on manager or employee role and, while performing the task at hand, your mind suddenly moves back to investor mode and thinks of something else that you want to accomplish at a very high level (like expanding to another market or creating a totally new business). At that point your long term goals and investor mindset takes over, derailing the focus of the other roles, consequentially stopping any progress that was being done on the tasks and eventually slowing down the whole execution. Eventually you come back to your other role and realize you wasted the whole day and didn’t get anything accomplished. The next day (or a couple of hours later) the same thing happens and you continue to be looped in that back and forth between being focused on short-term execution and thinking about big picture / long-term goals.

A solution to this problem is compartmentalization:

“an unconscious psychological defense mechanism used to avoid cognitive dissonance, or the mental discomfort and anxiety caused by a person’s having conflicting values, cognitions, emotions, beliefs, etc. within themselves. Compartmentalization allows these conflicting ideas to co-exist by inhibiting direct or explicit acknowledgement and interaction between separate compartmentalized self states”

The concept is simple and you can actually implement it by taking three steps:

1. Define the types of tasks or activities each role should take care of,
2. Breakdown your year/quarter/month/week/day into specific moments for each role to take over,
3. Establish proper communication channels between roles: Investor > Manager > Employee

That last step sounds crazy, right? Well, you have to be a little crazy to become a solopreneur.

A little more detail about what I mean with these three steps:

Define tasks for each role

Each of your internal personas should focus on different levels of the same issues. You start from 30,000 feet perspective for the investor/strategic role, going down to 15,000 for the manager/operational role and finally down to earth to the employee/execution role.

Decisions made by yourself under the investor role will then guide what the manager role will work on and that will guide the specific objectives and tasks that will be assigned to the employee role.

It’s very important that a lower level role (employee) doesn’t waste time trying to overthink or change a decision made by a higher level role (manager or investor). If you do that, then you will run into the analysis paralysis trap described earlier. When you are on employee mode just focus on “getting shit done”, leave the existential questions like “why am I doing this?” and big picture decisions for the other roles and just focus on getting your task done.

The right moments for each role

As a solopreneur, it’s inevitable to think and analyze the same thing from all three perspectives at once. However, you should resist that impulse and instead block specific times for focused work under each role.

Depending on the nature and stage of your business, the specific time and frequency of these may vary, but for example (just an example) I could organize this times like this:

• Investor role time: On the last friday of each month, block the whole afternoon (1–5pm) to assess long term goals, evaluate how your manager role is doing, see if anything needs to be adjusted or if there are some decisions that need your attention. At the end, have a one hour internal meeting with the manager role (in your mind) to communicate the decisions and see if there is any feedback and adjustments to be made to take it closer to planning.
• Manager role time: On the first monday of the month, block the whole morning (9am–12pm) to draft the monthly plan, making sure my boss’s interests (the investor role) are aligned with what we are focusing on this month. Then, define the specific goals and tasks, weekly milestones and key dates/deliverables to communicate to the employees (again, this is yourself now under employee role). As a manager, you should also have frequent touch-bases with employees, so aside from the monthly general planning time, you should have at least a weekly (or in some
  cases daily) management time blocked into your calendar.
• Employee role time: This is the time when you actually do, make, execute, generate something tangible… a deliverable. As an employee, you receive guidelines from management and then organize your day in a way that allows you to go through your to-do list and get things done. To be most effective, you shouldn’t ask “why” at this stage… just do. You know all of the thinking has been done before (by yourself as investor and then again as manager), so there is no point on delaying execution of the tasks by rethinking them at this stage… if you do that then you’ll fall into the analysis paralysis trap. If you think of ways to improve, better ways of doing things, new ideas, etc… send that to your manager (yourself) for analysis on their own time.

Establish the right communication channels for your internal personas

This could sound silly, since all of these roles are just in your mind and that means that the roles are always communicating with each other. However, it is important to avoid wasting time switching from one role to the other all day long.

The right communication channel depends on your specific preferences, whatever works for you is the right channel. For example, you could use a notebook (pen and paper) with three checklists: Strategic, Managerial and Daily-To-Do, a list per role. Then, any time you think or remember something you add it to the proper list. You then dedicate time to each item on the list when you are actually focusing on that role. What you want is to be able to focus on the right things at the right times.

If that doesn’t work for you, then use an app like Trello or Evernote. If that doesn’t work, send yourself emails with the role on the subject line (note to manager role, note to investor role, note to employee role).

Whatever works for you. The important thing it to capture all ideas and thoughts that fly over your mind so you can focus on them later, at the right time under the right mindset.

You will not be a solopreneur forever. This will prepare you to scale

You will not enjoy life if you remain a solopreneur working 18 hour days forever. At some point you will need to scale and all of this craziness of talking to yourself in compartmentalized roles will end.

You will actually get other investors or partners to join you, you will hire managers to take care of the operations and you will have employees that will take care of the day-to-day tasks.

Going through your initial stages as a solopreneur with this crazy dialog between roles will prepare you to scale once more people come on board.

Once new people come on board, you can finally start having conversations with real people and stop the craziness…