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Strategic Planning for Solopreneurs

Do you need to do Strategic Planning if you work alone? If you’re serious, you do. My Strategic Planning Retreat as a Solopreneur.

I had a hugely productive week last week. I accomplished a major milestone I had set for one of my brands. It took me maybe a week longer than I had targeted (including an all-day Saturday), but I’m so happy with the outcome that the exact completion date doesn’t matter. The work will continue to pay off for years with minimal load on my time.

This week I thought that project went so well, I would use it as a template and replicate it three more times. Then I started to think, well, I could do it a hundred more times, but what am I actually doing? I can do a lot of work, but specifically what end am I driving at? Am I really working in the right direction?

Doing the Right Work

In the late 80’s or early 90’s in college I recall asking a professor about a lower than expected grade on a homework assignment I had put a lot of work into. He said something along the lines of “Well, if your car needs new brakes, and you change the coolant, it doesn’t mean you didn’t do work. You just did the wrong work.” That stuck with me, maybe in part due to the sting of a sub-A or -B grade.

The same concept came in front of me years later when reading The 7 Habits of Highly Successful People by Stephen R. Covey when it first came out. I see it’s now on its 30th Anniversary Edition (groan). Anyhow, among lots of other undeniably great things Covey talked about the difference between leaders and managers. Super-boiled-down, my takeaway was that Managers make sure you’re doing the work right, Leaders make sure it’s the right work that you’re doing.

Fast-forward another 30 (really?) years to 2019. Discovery has a TV series called Undercover Billionaire. It’s about a self-made billionaire who bets he can create a company worth a million dollars in 90 days, using none of his contacts or clout, given only $100, in any random city the producers chose to drop him off on. The billionaire is Glenn Stearns; the name of his financial firm, Bear Stearns, may ring a bell for you. I’m glued to the TV for every episode. This I gotta know. I’m fairly certain I’m the only person in America with a composition book and a pencil, ready to take notes while watching TV. Five pages of handwritten notes, that’s what I ended up with. A lot of gold nuggets in there. Anyway, this lead-up is all to create a frame within to say that one of the phrases I wrote down was (and I may be paraphrasing here) “Don’t confuse effort with results. We all work hard, that goes without saying. It’s results that count.” The same message again!

I decided on Monday morning that I felt I was floundering about a bit. Like a man overboard dog-paddling in the middle of an ocean, I was about to start working hard yet not really knowing where I was going. I needed some strategy.

Executive Strategy Retreat for One, Please

It seems silly on the face of it to decide to have a retreat when you’re a solopreneur. A) If you retreat, who’s going to do the work? B) If you play hooky, you aren’t getting away with something, you’re cheating yourself. C) For most, you aren’t really going to go anywhere anyway. You’re going to be at the same desk, at the same computer you should be working at. It doesn’t feel right.

My advice is to get over that feeling if you’re having it. Back to Drucker, it’s time for Habit 7 – Sharpen the Saw. If you don’t improve your toolset, all the work in the world is going to approach zero usefulness. You have to know what the right work is in order to do the right work. You have to be a leader (in addition to a manager and a worker). Everyone works, it’s the results that count. A little time investment now is going to make the next several months or year soooo much more meaningful in terms of accomplishing the results you want to accomplish.

Don’t confuse effort with results. We all work hard, that goes without saying. It’s results that count.

Glenn Stearns, possibly paraphrased

I felt a little guilty at first, but it ebbed away over half a day as I started to get into the tough work of strategy.

How Do You Even ‘Do’ Strategy for a Solopreneur?

There are probably 10,000 pieces to developing corporate strategy. There are forms who are entirely based on helping you through their process of strategic planning. There are highly paid Chief Strategy Officers. Strategy can be a complex thing, sometimes taking abstract dreamy forms. I don’t have the time, money, or need for any of that.

I don’t have an HR department. I don’t have Corporate Communications, Marketing Communications, or Public Relations people. I’m an engineer at heart, and often in practice. I’m not one of those fancy-words types. In fact I shun corporate-speak, jargon. On the plus side, I don’t have a diverse staff of people with varying cultures, varying levels of expectations from management, and varying skin-thickness. There’s nothing wrong with having all that – it’s a true strength for every multi-person organization – I believe that 100%.

It’s just not the case where I work. Or where any solopreneur works. It’s just you. You’re doing strategic planning that only you need to be satisfied with, assuming you don’t have investors to please. Even if you do have investors to please, you should be demanding the same level of strategic planning from yourself that they would anyway. So, where to start?

I’ve worked in corporate America, public and private companies, for a few decades. I’m not unfamiliar with the trappings of strategy, I know what it looks like. I’ve done a bit of it myself. Nonetheless, I decided to hunt around and see what the mode d’jour was around corporate strategic planning these days. I may off, but the Balanced Scorecard seems to be the most widely-adopted practice right now.

I did a bunch of digging for resources on Strategic Planning. I had to shake my head the SBA’s website. I couldn’t find a prominent reference to Strategic Planning anywhere. There are templates for Business Plans, none of which even have a header for Strategy. Using Google I did manage to find a PDF called Introduction to Strategic Planning which is inexplicably both sponsored by and explicitly un-endorsed by the SBA all on the title page.

After digging long enough that I was only finding rehashes of the same old things, I started to distill my plan for planning. I decided I would shadow a 9-step process meant to implement a balanced scorecard in an organization over 5 months. I figured a day, maybe two.

Plot Spoiler: It turns out I only needed to go to Step 2, and never really got into the Balanced Scorecard specifics. For me, I had enough definition, scope, and detail to set course for the next 6-12 months. A day and a half investment.

The Fundamental Big Picture Stuff

I have a big giant plan of the specific things I want to get done business-wise that goes 10+ years into the future. I even have those efforts grouped into different ‘business units’ or ‘topical collections’ or ‘things that seem to make commercial sense together’ or whatever you want to call them. What I didn’t have was an overarching strategy, mission, vision, or set of values for each of those. I know, I just used some corporate-speak, but please stay with me for a moment longer – after all, you’ve come this far…

All I wanted was to establish some strategic goals, so that I could create tactical goals from those, and get back to work accomplishing the tactical goals. It turns out that strategic goals aren’t simply fabricated from thin air. They’re hierarchically based on something else, which is in turn based on something else. But instead of getting harder to do as you go up, it gets easier to create the high-level things that the strategic goals are based on. You can be less specific. You must be less specific. These higher level things are the Vision, Mission, and Values of the organization.

If you’re like me, you never put much stock in a corporate Vision or Mission statement. I figured the “C” Suite spent no more than 30 minutes on them, and therefore I wouldn’t spend more than three. They seem grandiose (“we all know that’s not happening any time soon”) or meek (“ok, we’ll give it a whirl and see what happens”), thick or hollow. They’ve never been inspirational or motivational to me. But then, I didn’t understand what they were really for, aside from decoration. It turns out these can be some pretty powerful concepts if you take them seriously.

The Hierarchy of Strategy

The strategy flows downhill from the Vision. The Mission is derived from the Vision. The next layer down is referred to variously as the “Focus Areas”, “Key Performance Areas (KPAs)”, or “Strategic Objectives”. It is from this third layer which the Strategic Goals are derived. Once you have strategic goals, you can create tactical goals to accomplish them. The Values describe the fabric from which all should be built throughout the hierarchy.

Organizational Strategic Hierarchical Elements

So, even for the solopreneur, it’s back to the corporate jargony sounding things just to figure out what the right work is to be doing today.

There’s a ton of information on how to develop these for yourself. Just search for the various terms and you’ll be inundated with pages re-spinning the same content as SEO bait for their sites. But there’s enough information there to get you going. I’m not going to insult you (or myself) by repeating it all here. I will indulge in a small overview though.

In a nutshell, your Vision is a few words to a single sentence that answers these questions:

  • What problem are we (am I) seeking to solve?
  • Where are we (am I) headed?
  • If we (I) achieved all strategic goals, what would this organization look like 10 years from now?

Your Mission is similar, but more specific. It’s a sentence, maybe even a long sentence. It answers these questions:

  • What is our organization’s purpose?
  • Solo-ized -> What value was I trying to provide people when I started this thing?
  • Why does our organization exist?
  • Solo-ized -> What’s the point of it being here, from an outsider’s perspective?

These are each only a few words. Every word is important. Open up a new document to use as a scratchpad, and just start brainstorming thoughts. You can trim, combine, swap out, and spend some time at thesaurus.com to put them all together. Do it right, make it meaningful and absolutely accurate. Your whole strategy will based on these, it’s important to get them right. That said, don’t let perfection be the enemy of progress. There won’t be a statue anywhere with these words carved into its base. It’s just you and you can make little adjustments later without impacting anyone else if you need to.

Your Values are what will define your culture. As a solopreneur, you’ll probably find your personal values strongly represented in your organizational values. I know mine do. But envision on-boarding your first employee and explaining these values to them, or presenting them to potential or actual investors. They’re for the good of the organization, not you personally. I ended up with 5 of them. And do you know what the last one on my list is? It’s “Don’t confuse effort with results…it’s results that count”, of course.

Other Valuable Strategic Planning Artifacts

Through the process, I did a few other exercises that I found had some valuable output. I recommend doing these too while you’re at your corporate strategic retreat.

Enablers and Challenges, or SW

For each brand I have operating, I wrote down three to five bullet points which are the strengths or enablers for that brand. These are the assets which that brand has (that I have, that are in the market environment today, etc.) which put it into a position to dominate. The Strengths of a SWOT analysis in other words.

I did the same thing for challenges. Things that are hard to do or hard to beat for that brand. These are basically the Weaknesses from a SWOT analysis.

When I say SWOT analysis, I mean a serious, things-that-matter-right-now SWOT analysis. Don’t put things in there like potential foreign policy changes or global economy trends or civil unrest in Myanmar – unless you’re particularly dependent on those things and change seems very likely coming your way.

Why do these? Where will you ever use them? Well, it just so happens I have an answer. These help you figure out if your Vision and your Mission are realistic. They might make you broaden scope in one direction or veer away from another. You might even pivot a little. It lets you know where the open road is, and where the proverbial 5-miles of bad road is.

Yep, Mile 5 of Bad Road. Been there. Took the pic.

Stakeholder Needs Analysis

Who are your stakeholders? They are your organization, and each of it’s customer personas. If you have investors, they’re stakeholders too. Your community might be a stakeholder, depending on the nature of your business. So make that list, and put yourself in each of their shoes for a few minutes. Write down what they want to get out of a relationship with your organization. They are coming to you looking for _______. They’ll come back if they get ______ this time. Those are their needs.

Where will you use this little gem of enlightenment? In setting up your strategic objectives for one. You want to give everyone what they’re looking for, right? The organization needs to get what you need it to get, and customers and investors need to get what they need. The strategic goals or objectives are what make that happen.

Also, you’ll use the needs analysis in creating a Customer Value Proposition. Which brings me to the…

Customer Value Proposition

You probably already have one of these, even if by accident. If you have a tagline, you have a customer value proposition. Maybe you didn’t mean for it to be that, but it is that. A Customer Value proposition is a promise of what you’ll deliver to the customer. It’s well worth developing this because you can use and reuse it bits and pieces of it in various forms and formats throughout your website, printed materials, apps, and whatever other branding and marketing visibility you have.

There’s a ton of advice on how to create a good customer value proposition out there, search away. My intent is only to endorse the activity of doing it and doing it right because I believe it’s another artifact that you can plug in and re-use in plenty of places.

Putting it All Together

It should take a day or two, maybe three to do this depending on the maturity and complexity of your solo organization. First get the big blocks like Vision, Mission, and Values in place. Then start looking at Enablers/Strengths, Challenges/Weaknesses, and Stakeholder Needs. I did the Customer Value Proposition last. By that time, I had a good idea of who the organization wanted to be, and what customers would be getting from it.

Create Strategic Goals (FINALLY) to support each of the Strategic Objectives / Focus Areas / KPAs. Strategic goals can support multiple objectives, and some objectives need multiple goals to accomplish them. That’s fine.

Once the Strategic goals are in place, you can create tactical goals with actual KPI’s to measure and real deadlines. Then map them out over the next 6 months to a year. Mine looks roughly like this (but with more detail):

Strategic on the left, tactical mapped out over time

Sorry it’s small, it should open up larger if you click/tap it. But you get the idea. The reason to map it out like this is to do some resource-leveling. At first, I had stacked up a lot of goals on top of each other. It’s just me, so that’s not realistic. Prioritize and distribute them realistically.

Once you have the goals evened out time-wise, you’re set. You can print this out and tape it to the wall above your monitor or in the kitchen or garage or wherever you work, and you’ll know every day what it is that you should be working on. You know you’ll be doing the right work. Now you can get back to doing the work right.

Enjoy the process!