SelfInformed

How Best to Take Time Off for the Self-Employed

There is a lot to love about being self-employed. Whether you sought out self-employment because of the freedom it would provide, or this is just naturally where your career ended up, most people who find success in self-employment can’t imagine working any other way.

If there is a notable drawback to mention, however, it’s the challenge of taking time off. Millions of self-employed individuals understand the struggle of trying to get away for a traditional vacation while building a business. It’s important to have strategies in place to make sure you can get the breaks you deserve while avoiding any harm to your business in the process.

The Fundamental Challenge

Self-employed individuals struggle to take time off because they are, by definition, putting work on hold while they do other things. Even if the business is doing well and things are good, this is a tough decision to make. What if a big opportunity comes along and you aren’t able to respond quickly enough to seal the deal? What if a long-time client has an urgent request and you can’t help out when needed? No matter what your business looks like, you’ve probably run over these various scenarios a million times in your head before taking any kind of time off.

It’s quite likely that some financial implications are going to result from taking time off and being away from your business. If you were only in it to completely optimize for income, you’d work as many hours per day as possible, and you’d never take a day off. But that’s not a sustainable lifestyle, either personally or professionally. So, it’s necessary to adopt a mindset where you willingly miss out on an opportunity for additional revenue in order to give yourself the break you deserve.

Start with Strategic Thinking

To successfully take time off while having the least possible impact on your small business, you need to think strategically about how you are going to do it. The sooner you can do this thinking, the sooner you’ll be able to start taking time off at regular intervals – and doing it in a way that you feel good about.

Here are a few points to guide your thinking when crafting a vacation strategy –

• Consider seasonality. If your business is naturally seasonal, the variation in your schedule throughout the year gives you a big opportunity to take vacations with minimal stress. Plan to take time off during the quieter time of the year and expect to work a lot during the busy season when it’s all you can do to keep up with everything that’s going on.
• What’s a reasonable duration? It might be possible to take a full week or two off without too many problems popping up, as long as you plan properly. On the other hand, for some self-employed people, that just won’t be feasible. If you can’t get away for a full week, think about planning multiple vacations that last just three or four days each.
• Do you have to stay in touch? It would be great to completely disappear for a while and reset, but again, that won’t be a practical option for some people. Choose your vacation destinations based on whether or not you’ll need to check in on things and communicate with people while you are gone. The cabin in the woods without cell coverage or Wi-Fi might look great, but the harm that such a trip could do your business might not make it a reasonable destination.

Mastering Clear Communication

It’s your ability to communicate clearly that is going to make or break the whole vacation experience in this situation. If you properly explain your upcoming schedule to clients and customers, and everyone knows when you will be gone, it shouldn’t turn into a big deal. If they have no idea you’ll be unavailable, however, and then you just disappear for a while without explanation, things could go south.

As soon as you plan a vacation, provide information to clients or customers about your upcoming absence. The way this looks will depend on your specific situation. If you only work with a small handful of clients, and you work with each of them regularly, send out a quick email to the client list ahead of your scheduled break so they all know what is going on. Rarely will anyone take issue with you taking a break as long as they know it is happening.

Honesty is the best course of action when taking a vacation. Don’t try to hide the fact that you are taking time off from your clients, hoping you can hide your absence and get back before they are any the wiser. That might work once or twice if you are lucky, but it will catch up to you eventually. Instead, just be upfront with your plans, explain when you’ll be available, and build your relationships based on honesty and trust.

Preparing Your Support Team

First, it’s important to say this – the advice in this section won’t apply to everyone. If you are a solopreneur or are just starting a business and are the only person involved in the operation, there is no support staff and these tips don’t apply.

However, many people who are self-employed do have employees or contractors that they work with to serve the needs of their clients or customers. In this situation, you’ll want to have detailed instructions for how certain situations should be handled while you are gone. Do you want the team to make key decisions for you, or should they reach out and ask for a bit of your time when something comes up? Creating a checklist or a couple of different checklists for how scenarios should be managed can put your mind at ease and make their lives easier while you are gone.

This is also a great time to encourage some of your team members to step up and play a bigger role in the business. Given an opportunity to show what they can do when forced to take more responsibility, you might find that someone on your team has more to offer than you realized previously.

Create a Time-Off System

It’s common for time off to not be entirely “off” for a self-employed business owner. For example, even if you are out of town and won’t be working for a week, you might end up spending a bit of time on your computer each day, checking in on things and solving problems.

To do this without ruining your vacation, create a system before you leave that determines how and when you are going to do a bit of work. As an example, imagine you are taking a trip to the beach with your kids. While you are out playing in the sand, you don’t want to be staring at your phone or dealing with work problems. So, unplug during those times and be fully present in the moment.

You won’t be on the beach for the entire time, however. After a session playing in the sand, you’ll go back to where you are staying so the kids can rest up and get ready for another adventure. Maybe you plan on these afternoon breaks as a good time to take 30 minutes to check in on work and respond to some messages. That would be a modest footprint that doesn’t destroy your vacation but keeps work on track at the same time.

Keep Your Long-Term Vision in Mind

Most likely, you already have a long-term vision in mind for where you want your business to be in 1, 5, 10 years, or more. It’s easy to get caught up in working so hard toward that vision that you lose track of what is going on currently in day-to-day life. True success achieves a balance between personal and professional pursuits, as prioritizing one too much over the other is rarely going to take you where you want to go.

Remember, burning out and losing interest in your business is not a part of your plan. And that’s where you’ll likely be headed without prioritizing time off periodically. By using some of what we have talked about so far, including creating a system for when you are gone and communicating clearly with clients and customers, you should be able to find a plan for vacations that works for all involved.

Learning from Your Mistakes

Despite your best efforts, be realistic about the fact that some mistakes are going to be made along the way. Everyone makes mistakes in business, and issues related to vacations are common. So, once you do start to take regular time off, you might find that some things go wrong at the start and need to be corrected.

Issues coming up while you are on vacation don’t mean you should stop taking vacations – they mean you should revise your systems and figure out where it went wrong and how you could make it better next time. Just like you consistently refine your systems for marketing, sales, and more, you will need to refine your vacation system to the point where it is a well-oiled, reliable, and effective machine.

Conclusion

Is it possible for a micro business owner or other self-employed individuals to take time off? Yes – absolutely. While it might not be as simple as just turning in a vacation request to your boss and marking those days on your calendar, you can make it happen. Utilize some of the strategies discussed above to find yourself with more days off in the year ahead.

Republican Trifecta, Nominations, First 100 Days, and Trump-Vance Priorities

Senate

The Republicans have secured the majority in the Senate, picking up crucial seats in Montana, Pennsylvania, Ohio, and West Virginia. Democrats held their own in Arizona, Nevada, and Wisconsin, helping keep the majority slim.

Speaking of vacancies, Governor Mike DeWine (R-OH) will appoint to fill the vacancy by Vice President-elect JD Vance. The timing is TBD based on when Vice President-elect JD Vance formally submits his resignation, probably some time closer to inauguration.

House 

The Republicans have clinched the majority, although a slim, razor majority of somewhere between 1 and 5 seats. The slim majority is even tighter due to three nominations of current House members to serve in the Trump Administration: Rep Matt Gaetz as Attorney General, Rep Elise Stefanik as UN Ambassador and Rep. Mike Waltz as National Security advisor.

House Leadership

Speaker Johnson (R-LA) and Majority Leader Scalise (R-LA) have both publicly announced they will seek to retain their leadership roles. Given the trajectory of the 2024 election outcome, it would be surprising to see a member of the caucus challenge either one, but again, slim majorities make for interesting times.

Leader Jeffries and his team should remain intact, although there is a significant (understably) assessment of what went wrong. In fairness, the Democrats were fairly bullish on their predictions to gain control of the lower chamber, but it is still something the conference needs to contend with.

Senate Leadership

On November 13, Senate Republicans elected Senator John Thune (R-SD) to serve as the next Republican Leader of the Senate. Sen. Thune won the leadership election against Senators John Cornyn (R-TX) and Rick Scott (R-FL) in a secret ballot election. President-elect Trump did not endorse a candidate in the Leadership race at the advice of allies in the Senate.

Trump Nominations

Attorney General: Congressman Matt Gaetz

Secretary of Defense: Pete Hegseth

Secretary of State: Senator Marco Rubio

Secretary of Homeland Security: Governor Kristi Noem

Secretary of Interior: North Dakota Governor Burgum

Secretary of HHS: RJF Jr.

EPA: Former Congressman Lee Zeldin

National Security Advisor: Congressman Mike Waltz

UN Ambassador: Congresswoman Elise Stefanik

US Ambassador to Israeli: Former Governor Mike Huckabee

DNI: former Congresswoman Tulsi Gabbard

First 100 Days

Executive Orders

It is believed that over 300 executive orders (compared to President Biden: he signed 34 EOs in the first four months of his Administration) have been prepared for President-elect Trump to take action on, usually the bulk of EOs are utilized to rescind action of the previous Administration. However, there are some highly unique positions that we could anticipate via Executive Orders, including:

Immigration Policies

Reinstating the Travel Ban: The administration plans to reissue the travel ban affecting several majority-Muslim countries, a policy first implemented in 2017.

Halting Refugee Resettlement: An executive order is anticipated to suspend refugee admissions, aiming to reduce legal immigration pathways.

Government Restructuring

Reimplementing "Schedule F": Would make it possible for agencies to reclassify certain career federal workers in policy-related roles to a new “Schedule F” category of employment. Any employees moved into the new Schedule F classification would have seen their civil service protections removed, making them at-will employees and giving agencies much more flexibility to fire them.

Climate

Withdrawal from the Paris Climate Agreements: In the previous Trump Administration, the US exited the agreement. However, President Joe Biden signed a letter requesting the US be readmitted on his first day in office. Many anticipate that Trump will once again move to exit the agreement. Leaving the agreement would mean the US is no longer beholden to meeting set carbon emissions reductions.

Tariffs

Across the Board Tariffs: Trump’s plan includes imposing tariffs on imported goods, especially those coming in from China, arguing that these taxes would keep manufacturing jobs in the US.

It’s still unclear how widespread these tariffs will be, but Trump has raised the prospect of at least a 10% across-the-board tariff on imported goods, as well as a 60% import tax on goods from China.

Trump-Vance Administration Priorities

Taxes

We anticipate in the first 100 days for Congress to advance via reconciliation an extension of the Tax Cuts and Jobs Act. This act significantly reduced corporate tax rates and provided tax relief for high-income earners. While there is unlikely to be major opposition to the extension of some of the provisions, Republicans have voiced concern related to the impact of the growing federal deficit, which could set up a very brutal fight around offsets and discretionary spending.

Regulatory Action

The Trump Administration will focus heavily on reducing regulatory burden and rolling back Biden era rules in the banking, financial services, and housing sectors; as well as repealing environmental, social, and governance (ESG) and climate disclosure standards (EO 14030).

Small Business