Editor’s note: This is a guest post by Jenn Labin. It has been updated from the original published version to include links to the Momentum app.
I’ve spent more than half of the last 20 years working as an entrepreneur and consultant. I was very happy with all of the amazing benefits of that work. But I am now starting a new adventure, one of going back to employment for someone else. The decision is a very good thing for me and my family. However, I know enough about the impact of transition (see the research here) to expect the change to have an emotional side.
To prepare myself for the transition and its emotional impact, I’ve spent a few days thinking back on my tenure as a business owner. There are some wins, but it’s easy to dwell on the failures. And do I mean FAILURES! Whew, there are some things so powerfully negative that when I think about them I suck air through my teeth, like when you get a paper cut. But I’ve learned from those entrepreneurial mistakes and failures. And if I can share any of my experiences that helps just one of you not have those negative feelings, well, I’ll be happy with that legacy!
Without further ado, here are my thoughts on the five mortal sins of entrepreneurship.
5. Fade Away
The “fade away.” I think every RomCom has an episode of this. You don’t want to hurt someone else’s feelings, or you’re embarrassed about something, so you don’t reach out or respond. Ever. Again. You pray that the other person just moves on and forgets you existed. That’s fine for a RomCom. But, goodness, the professional version of this is a reputation killer.
Example: You have a project deadline for “Customer A” of May 1. You’ve worked hard on the project, but other projects start blowing up and you’re forced to delay your work for Customer A another week, another two weeks. Eventually you reach a point where you think, “Okay, I’ll work all weekend to get it done and apologize when I send it in Sunday night.” Then, family obligations prevent you from finishing, so you’re back to more delays. Now the project is overdue by a month and is just embarrassing! What do you do?
I can remember three times where I faced an extremely late project, failed to communicate the delays, and had to decide what to do.
In all three situations, I had very legitimate reasons for what happened. In one situation, I hired and then lost three different experts to execute on the work. I ended up having to do all of the work myself, months later than expected.
In another situation, the customer tried to change the project scope drastically (more on that later), and tried to bring in about 15 people to approve each tiny step forward. Their internal approval process created such massive delays, I had to try to complete this work after I had already started a brand new massive project.
In two out of three cases, I went back to the customers on my knees and gave an honest accounting of what happened—without making excuses. Both of those customers were understanding, but I didn’t ever get the opportunity to work with them again. The third customer was the one I still cringe when I think about, because I never did get to a resolution with them. By the time I was able to pick up the work and finish the project, the deliverable was not going to be useful to them at all.
What to do when you face a similar situation? I can only share what’s been successful for me. Even though I still have a tendency for magical thinking (“This week I’ll have time to work on it for sure!”), I try to be more communicative. It’s never an easy conversation when you have to admit to mistakes, and you still might lose that customer, but it’s far better than fading away and worrying if it will come back to bite you in the rear later.
4. Try to Do Everything
When I started working with Charlie as my business coach, one of the first things he asked was if I had someone to clean the house, babysit the kids, and cook meals. He was gently nudging me toward a truth: an entrepreneur’s life is pretty much always chaotic. You should find other experts to do the things you don’t need to be doing. From a work/life standpoint, that part was easy for me. (I’m still looking for a housekeeper who does laundry in the Baltimore, MD area if you know someone…)
The same idea applies to your business, which was a tougher lesson for me to learn. I wrote the updates to the website, tried to manage the social media accounts, kept the CRM up to date, handled all of the sales calls, wrote the proposals, sent the invoices, collected payment and managed the accounting software, hired, fired, project managed, booked travel, set calendar appointments … Oh, yeah, and I did the work my customers were paying me to do! My focus was constantly fractured. It was difficult for me to justify paying others what I thought of as a high rate to do work I could do for “free.”
The same challenge can also happen with the kind of work you accept. My focus is on mentoring programs and mentoring skills. But two years ago I took a project to create an eLearning course on Laboratory Safety. I actually just physically shook my head at writing this mistake down. It’s so difficult when you are building your business to turn down work. Walking away from dollars feels like hubris, like idiocy, in the moment. In actuality, though, lots of really smart people have written about the long-term impact of going outside of your focus area and how detrimental it can be to your business.
So practice saying, “No.” Think about your long-term vision of success for your business. Are you the person sending invoices? Probably not. Are you taking work vastly different from your core sweet spot? Nope. Make decisions now that mirror the future you want.
3. Fail to Define Scope and Expectations
I am known for coming up with great ideas too difficult and complex problems but not so much the details and procedures. It never felt very important to create rigid, documented project scopes and expectations. Well, I was utterly and completely wrong.
I firmly believe that the reason people get disappointed is that their expectations aren’t met. The easiest way to not meet expectations is to not discuss explicitly what those expectations are. Over the years, I’ve gotten better at trying to proactively identify the risks of scope creep, though I’m always working to improve. In project work, that means spelling out, in detail, guidelines like:
- When are deliverables due?
- In what formats?
- How many revision cycles are within scope?
- How many customer approvers are expected?
- What happens if there are client-side delays?
- What happens if there is a request to increase scope or level of effort?
- When are payments due?
- What happens if payments run late?
- Who owns the deliverables?
Since my work is in consulting, I started to learn how to have these conversations early on after several customers were surprised when I sent them a slide deck or a PDF with the deliverables. I’m still not sure what they were expecting. Maybe they weren’t, either.
You also need to identify roles in your work. That is, spell out your responsibilities and the customer’s responsibilities. Get agreement on these! If there is more than one customer contact, divide up the responsibilities visibly so that you know whom to contact.
2. Under Deliver on Your Promises
I don’t think I know anyone who intentionally says they will create some great thing, only to deliver a completely underwhelming version. But when it does happen, it’s pretty much a deal breaker that could hurt your current and future reputation.
Under delivering happens when:
- Expectations of work product are not clear on both sides (see above)
- You run out of time/bandwidth and have to deliver a sub-par product
- You attempt to share a draft, with the intention of improving it, but never get to the final
The fix for this kind of scenario is easy. Set clear expectations, and revisit those expectations when you need to. Communicate clearly about delays, revisions and edits, and customer-side issues.
Finally, if you want to follow an iterative design process, do so openly. An iterative design process is one where you submit drafts of the work product in very raw form (think 50% done), then go through many, quick revision cycles, improving it about 10% each time. Speak with your client about this work style and manage it closely.
1. Over Schedule Your Time
Over-scheduling is the BIG one, at least for me. This is “magical thinking” at its finest. It says I am a capable, hard worker, so surely I can get that task done in a reasonable amount of time. The biggest problem here is that when you are wrong about how long it will take you to complete one task, the miscalculation cascades and affects everything.
If you are a creative entrepreneur — an artist, writer, photographer, etc. — this may be even tougher for you. How long does it take to write a book chapter? I’ve published two non-fiction books. The first one took three times as long to write, and it was half as long.
In my case, I’m great at estimating how long a task takes objectively (90 minutes, 8 hours, etc.) but terrible at taking the rest of my life into account. A 90-minute task might take me five days to complete because my kid gets sick, another customer’s project blows up, my dishwasher breaks, my internet goes down, or my files refuse to upload. You get the picture.
I believe that if I had been able to master this time management skill years ago, my revenue would be several times what it is today. Accurately predicting how long a task will take, within the landscape of all of my other tasks, is a way to avoid all of the other entrepreneurial mistakes I’ve discussed in this post. Customers may not be happy if you can’t put a rush on their work, but they will appreciate you delivering exactly what you discussed when you said you would.
I’ve heard different ideas for combatting this time management issue. I worked with one graphic designer who would never commit to getting a task done in less than two weeks, no matter how small. One of my mentors has a “1.3 rule.” She multiplies how long she thinks something will take her by 1.3 and tells the client the inflated due date to give herself some wiggle room.
Those are great solutions, but the only tool that has worked for me consistently is Momentum. I can tell you from years of self-observation that my ability to accurately predict the pace at which I can accomplish tasks is exponentially better if I’m using Momentum. Every time I start to tell myself I don’t have time to slow down and set up my plans, or maybe I think I’m really clear on the couple of things I have to do and don’t need the planner, my life turns into chaos.
Momentum constrains how many projects and tasks you can plan to tackle in a given time period. When you have something new to add, it’s immediately clear what gets displaced, so you can react appropriately. There’s an entire process to using Momentum, so check it out here.
The 5 Essential Skills
How do you get really good at avoiding the five mortal sins of entrepreneurship? You master the 5 Essential Skills of Doing Your Best Work. Learn to look forward and visualize, which will help you to avoid doing everything. Chunking big tasks into smaller, manageable pieces of work bypasses the issues that lead to underdelivering and fading away. Prioritizing and sequencing are skills that, when practiced regularly, help you manage your time well, and set and meet expectations. Articulating goals well helps you open up communication with and set expectations for your customer, and manage your overall work process. (Tweet this.)
Above all else, spend some time figuring out what behaviors might be holding you back from your long-term vision of success. What tendency or behavior is getting in your way? Look to tools like Momentum, resources like the 5 Essential Skills, and communities like the PF Free Community to support your work.