Boundaries Between Work and Side Hustle

Many of us, if not most of us, have side projects from time to time. Whether we are doing development work after hours, running a side business selling products, or just doing creative work (like this podcast), side projects come with a number of challenges that can cause problems at work. In particular, you have to be very careful that not only does your side project not interfere with your day job, but that it doesn’t even appear to do so. Additionally, if you want your side project to be successful, you also have to make sure that your day job doesn’t interfere with it in a way that causes it to fail. This balance can be very tricky to maintain.

These problems are especially painful for side projects that are actually generating revenue. While you may have hobbies and other interests outside of work, employers are often more understanding when you casually mention them in conversation, or can’t stay late because you have a game. With side hustles, employers are very likely to take offense that they even exist, much less that you aren’t willing to throw them away for “the sake of the company”.

It’s vitally important, both to your day job and any side hustle that you have going, that you set appropriate boundaries and expectations. This can be a tricky tightrope to walk, as problems can occur during work hours with your side hustle, and work can sometimes have obligations and emergencies that impinge on your ability to meet your goals with your side project. Problems with your side project that interfere with work can get you fired, so it’s important to keep clear and consistent boundaries between them.

Keeping your day job and your side project from interfering with each other takes a lot of practice. There can often be conflicting priorities between the two that you’ll need to navigate in order to be successful. You shouldn’t let your employer destroy your side projects, but you cannot let your side projects interfere in work either. If you truly want to run something on the side, it has to survive long enough to make a living. However, you still have to eat right now. You have to play the game intelligently, or you’ll find your day job and your side project at odds.

Episode Breakdown

Deciding when/if to disclose your side project.

There is no real reason for your boss to know about the project at all. In fact, disclosing side projects to certain personality types can often make them blame your project for their own failings. You should carefully consider why your boss and/or coworkers even need to know about the side project in the first place before disclosing it.

If you do disclose it, you need to be extremely cautious about the timing. Don’t do it when the company is having cash flow issues or other problems, because it makes you a target. Feel free to do it only when the company is doing well and the market for developers is tight.

Also be extremely cautious about your “why”? Don’t tell them you are doing it because your day job sucks, especially if your day job sucks. Rather, it’s an opportunity that might yield a little cash, but will also help you build skills for your long-term career. Be careful about the information you disclose as part of “why”. You don’t want them thinking you are looking for another job when you aren’t

Deciding what to disclose about your side project.

If you do bring up your side project, be very careful with the information you give out. This is doubly true if you are close friends with people in your office, as people that are happy for you will spread good news faster than anyone else. You should also never give numbers to anyone.

Do not bring up your side project in unrelated conversations.You don’t want to look like you are selling something on the clock.

Never talk about your side project with clients of the company, in the presence of clients of the company, or in a place where you can be overheard by the same. This can lead to conversations that make it look like you are trying to sell to clients, which is an easily fireable offense in many places. This is precarious even if the client isn’t a potential customer of whatever you are selling, as they may still get it in their head to try and hire you away from your employer. It also looks really unprofessional.

Use of company resources/time/personnel.

Never give the appearance of using company equipment for your project. This includes printing, using your work desktop for writing code for your project after hours, etc. If you have to use your lunch break to work on something, bring your own laptop in and tether it to your phone. For your side project stuff, it’s better to create a completely different profile and everything, so that your passwords and bookmarks aren’t even available on work equipment. The only exception to these rules might be the use of a personal email account (if allowed) that occasionally gets messages related to the side business. However, while often allowed, it’s not a good idea.

Similarly, never give the appearance of using your coworkers’ time while on the clock for your project. This means that if you have a really nasty regex issue that the girl down the hall can fix in like five seconds, those five seconds don’t need to be on the clock. It’s probably ok to rarely ask for help on something, but don’t even let the request cross company equipment or occur in the building.

You should also be careful about being in the building at odd times. If anything does happen, this makes you (and your side hustle) a target, even if you aren’t doing anything unethical. Remember, it’s not whether they can prove anything, it’s whether they can waste your time and give you a headache trying to prove something.

These suggestions sound paranoid and sound like a person should treat the office as hostile territory. The idea is to keep it from being hostile territory. Lack of caution has caused problems for a lot of people. It’s also easier to enforce solid boundaries on work-related stuff if you aren’t bringing your stuff in to work.

Keeping the company out of your stuff.

Part of the reason you don’t want your stuff on company machines is that it means that you have to trust the company. Your network administrator (or any intruder on the network) could easily install a keylogger. They could also change your password and utilize any saved passwords you have on the system. They can also screen capture and monitor network logs to see where you are going and what you are doing online. While it’s unlikely that a reputable employer would go to the effort of doing something illegal, if your employer did damage your side business accidentally, and it harmed your customers, the cost might land on you.

You also want to keep them out of your time. You should try to have specifically scheduled times after hours when you work on side hustle stuff. This structure is usually necessary to make side projects work well anyway. You should also try to keep your employer from scheduling this time. This doesn’t mean telling them that this is your side project time, but rather that you have other plans.

You may have to be willing to compromise a little on your side project time, especially if there are emergencies at work. However, emergencies should not be a normal state of affairs. If you find your side project time regularly eaten up work, you either need to reschedule it, push back on work for using up your time, or find another position. Do not let a job, however good it is, destroy the time you need for side projects if your goal is owning one. You shouldn’t do a side hustle unless you are motivated to spend the time it takes to do it. If you are that motivated, you don’t let a random member of management destroy that. Particularly passive-aggressive managers will sometimes try to set things up to damage your side hustle if they know enough about it to do so. Don’t let them.

This also means not allowing work to damage your emotional state such that your side hustle suffers. This can be really difficult if you have management that is abrasive, overworks you, or where your environment is unpredictable. A good way to mitigate this if it is a problem is to get up early to work on your side hustle, so that it gets your best attention.

When something goes wrong in the side hustle.

If you have people paying you for something and there is a problem, then you probably are going to be expected to solve it fairly quickly. In general, if you bring a laptop in to work with you and try to correct such problems during lunch, you at least have a bit of wiggle room. You probably shouldn’t take “lunch” at a weird time to try and solve problems on your side project, unless they are extremely critical.

The processes on your side project need to be tested very thoroughly before being rolled out. While you may be in the habit of insufficient testing in your day job (lots of folks are), that will not work on a side project while you have a full-time job. Testing doesn’t get rid of all issues, but your goal here is to reduce the odds of having a problem while you are chained to a desk at your day job.

You should think carefully about when you do deployments. Deploying on Sunday night before a work week is probably not a good idea. Friday at lunch or Friday evening when you get home is probably smarter. Before particularly large deployments, sales, and the like, you may want to actually schedule a day off to handle any issues. If you do schedule a day off, don’t mention the side hustle as a reason. It’s a vacation day, nothing more.

When something goes wrong at work.

Most of us have had things go wrong at work. Sometimes this interferes with side project work. This could result from a client system falling over after hours. It could also result from a project manager packing too much stuff in during a sprint, forcing you to stay late to finish it. It could also be due to deployment/maintenance windows that occur after hours.

You need to have a fairly flexible schedule in regards to your side projects. This means that you generally can’t promise customers an exact time when a deployment will happen, a change will be made, or an issue will go away, because your day job takes priority. If work does have you working after hours, you should be getting compensated for it, or at least getting flex time. If neither, you need to make that happen or find another job that is more accommodating.

Continuous emergencies. Some jobs are always in a state of emergency, because management can’t manage. These are emergencies in the same sense that running out of gas is an emergency – it could have been avoided generally. Be careful about subsidizing your employer’s bad habits by damaging your side hustle. They will not return the favor. If you are considering a side hustle and have an employer like this, we suggest changing jobs first.

When you need time off for the side hustle.

Be honest, but don’t leak information. You should be able to take vacation days, especially when planned well in advance, without justifying them to management. It’s harder (from an HR perspective) to deny someone time off because they need time off than it is to do so because they are working on a side project. If they ask though, don’t lie. Lies get discovered and cause problems.

Some time-off events may proceed you resigning your job. If you are close to breaking free on a side hustle, and landing one more client, you may come back from a sales visit to that client and need to turn in your notice of resignation. Be sure if you do this that you communicate well with both the client and your employer. Give the employer enough time to come up with a way to transition. If you do this well, not only will you not burn bridges, but your employer will (generally) appreciate that you were considerate enough not to cause a problem for them.

When to think about leaving your day job.

You also need to have a clear picture about when to leave your day job for a side hustle if that comes up. Even with a bad employment situation, you probably don’t want to suddenly quit without notice. Since side hustles are risky, you should quit in such a way that the employer would welcome you back if things don’t work out. It’s also possible that your employer is a future client. You’d be surprised how often that happens.

Your understanding of when to leave should take your finances into account, unless you have another plan to make money in the interim. You also don’t want to leave without at least some percentage of your current salary coming in as revenue. If you only have an idea and don’t have revenue, you’ll be shocked at how long “good ideas” take to implement while your bank account is draining. It will also help you leave in a good way if you are running towards something rather than from something.

You should also try to time your exit better than other employees, because you can if you’ve taken your finances into account. This means trying to make sure that your exit doesn’t cause problems with any major deadlines (tradeshows, for instance) that are coming up. You should generally try to protect your team when you leave, whether you like them or not. Having money coming in on your side project(s) will help you do that.

Book Club

Power Talk: Using Language to Build Authority and Influence

We’re into the heart of the book now. Chapter five looks at transitioning between the two language types. In the beginning of the chapter she discusses several scenarios where you would start with one type of language and transition into another such as when starting your first job you want to start from the edge as a beginner. As you grow you’ll transition to a stronger knowledge base and have more centered language as your comfort and authority on the subject matter grow. In the latter part of the chapter she describes leadership and what it looks like to be a leader. Chapter 6 delves into electronic communication. This book was written in 2001 so it’s a fun look at the history of communication as it is pre social media {well we had MySpace and LiveJournal…don’t get me started…}. iPhones were still 6 years away when this was published. The information on emails is useful as most of us still use email at work. However we’re not sending messages to beepers and few of use really use fax anymore. The last section on backstage glimpses is still relevant as we should monitor our communication and how we present ourselves electronically.

Tricks of the Trade

Write a resignation letter the first time you consider leaving and then keep it for a while. Change the wording each time you feel the urge to bail. This gets the emotions out of the equation and also lets you determine whether it is a bad day or a bad job. You might be surprised at how often you are wrong about which it is.

Tagged with: , , , ,