Switching Hats: the Ultimate Entrepreneurial Test
By Liane Sebastian, Graphic Designer and Author
I. Entrepreneurial Basics: Multiple Roles
Although everyone longs for simplicity, very few ever achieve it. Certainly gone are the days of single career pursuits! Gone also are the days of corporate loyalty and defined growth paths. To flourish in the complex blend of physical and cyber business, an expanding range of professional skills are needed. The independent business owner knows she must shift seamlessly between different roles, or hats, or even between different outfits! How can the necessary business costumes be changed efficiently?? Comfortably? Easily? Even simply?!? Here are ideas for leveraging roles effectively:
- Batch or group related activities together such as phone calls, emails, meetings, bookkeeping, errands or sales activities.
- Prioritize activities that accomplish more than one goal. Any task that will fulfill multiple avenues of progress will make each pursuit more powerful.
- Accept as undone what is lower on the Things to Do list. No one can do everything on her list anymore. Some projects never finish! This is difficult for those who love the sense of accomplishment—it is hard to believe that a list can never be all crossed off. Realistically, a person can only do about six things a day. Each morning, Mary Kay wrote down the six most important tasks of her day and worked to get those done. The rest can wait. (Her tradition is still practiced in her company even after her death.)
- Abandon perfection. In today’s fast-paced business environment, perfection is mostly a luxury. The line needs to be drawn on what polishing affects the final reception; if further work will matter to the ultimate audience or purpose, then it is worth doing. If no one will notice the improvements, then they aren’t worth taking the time.
- Curb bad habits. This is the first key to an attempt at simplification. Though life gets more complex, the only defense is to attack the biggest time-wasters. Interruptions top the list for most professionals. The trend to work at home allows for greater blocks of focus-time (if work has a separate space from family). With an outside office, though a closed door may be unpopular, if done strategically, staff and colleagues can adapt if they see greater productivity!
- Master auto-response technology. Most people receive categories of emails. Templates can speed up messaging and let the sender know what to expect.
- Learn the preferred modes of communication for each colleague. Every mode has advantages and disadvantages—discover and perfect the craft of interactive communications.
- Use your strengths. It is a fact that each entrepreneur can’t do all that needs to be done and can’t be good at everything. Playing to strengths and compensating for weaknesses is the only way to stay sane. The difference between opportunity and distraction is in how strengths are maximized.
To juggle best takes management and coordination, much like a symphony conductor. Too many competing demands causes a dischordant reaction. To be proactive means to develop control and a perspective of potential while keeping and communicating realistic expectations.
II. Advanced Entrepreneurial Hat-switching: Multiple Revenue Streams
Not only is the entrepreneur’s Things to Do list longer than it was in pre-Internet days, the technology raises expectations. It isn’t enough to be a designer or a writer or a financial advisor. Today, like out of a Woody Allen movie, professionals introduce themselves at cocktail parties: “Hi, I am a professional whatever, with my book How to Whatever.” Financial success equates with a new form of pontification that was at first additive and is now mandatory to a career. Anyone who knows anything writes a book. It may not be a very good book (most aren’t) and it may be an ego-trip (usually is) and has a short shelf life (if one at all). Self-publishing grows at an alarming rate—yet only 20% is any good and only 2% will become successful. It seems, though, that if every entrepreneur hasn’t written a book, each wants to!
This places the entrepreneur in the position of cultivating multiple revenue sources—often interlinked like a plate of spaghetti. Navigating all the elements of a successful business becomes magnified. To paddle on this river of change, both new tools as well as new criteria are necessary to prioritize. Here are some ideas to begin discussion:
- Discriminate. Don’t undertake a new revenue opportunity unless it directly cross-sells to the major business focus, strength, and momentum. It is easy to get distracted by parallel disciplines such as teaching, craft production, or new product creation. Parallel businesses usually need partnerships and to be defined as separate ventures. Any new venture is difficult to develop in parallel with a first and ongoing commitment. Generating great ideas is easy compared to implementing them properly without the right help!
- Learn the art of the flexible schedule. Especially in a service business, deadlines place workers in reactionary modes. No schedule weakens productivity as much as a strict schedule that can’t bend to demands. Finding ways to move around activities and responsibilities is the way to weave various business segments. Commitments that lock in dates must possess the greatest opportunities, or exercising a “no” response is appropriate.
- Economize on time. In addition to being flexible, planning is always necessary for finding shortcuts. For example, going to a meeting off site can be best scheduled in conjunction with another event or errand. Travel may encompass more preparation time, but save on the number of trips.
- Master multimedia blending. Use various communication forms for what each is best at accomplishing. For example, an underused—and often misused—contact vehicle is Voice Mail. Because it is only one-way, the message needs to be extremely short and grabby. Similar to the subject-line for an email, every word used in a voice mail is important. Similarly, printed mail can be used more visually because drives detail investigation to the web. Once attention is captured, interactivity can be encouraged.
As a graphic designer and writer, for me discovering opportunity is like attending a banquet of possibilities. To generate a new idea is as easy as breathing. Yet, making the most sense of the options, focusing on what I can do uniquely, and maximizing my strengths seem much harder than in the past. Never has the entrepreneur lived in a simple business environment. Yet the opportunities were simpler 20 years ago. What technology has done is make my plate fuller. To avoid indigestion, developing skills to edit, develop, and leverage have become managerially mandatory. So the past doesn’t help on making sense of this new frontier. New variables need to be examined from the vantage point of blending purpose, priority, and values. Escalating hats, outfits, and wardrobes are necessary for the new business climate—how each chooses to wear them is how mastery is redefined.
Liane Sebastian is a graphic designer and author of Digital Design Business Practices (Allworth Press, NY) and Idea Initiators (Prosperia Publishing, Evanston). She is also the chair of NAWBO Chicago’s Creatives Special Interest Group and sponsors the monthly CreativiTea program.


