Painful Lessons I Learned In My First Two Years In Business

Sabreen Ahsan

This article was first published on Medium on Sep 14, 2020

Raise your hand if you’ve ever forgotten a birthday or an anniversary.

I confess that this year, I let a pretty significant milestone pass by, without acknowledgement: in May 2018, after two and a half years of freelancing, and six months of ‘making sure it was just the right timing’ (spoiler: there’s no such thing), I officially launched PIYA Media, my digital marketing agency. It seems undisputed among business experts that the first two years in business are always the hardest. In fact, this warning is repeated to new entrepreneurs so often that I’m sure it loses its full impact; these simple words fail to cover the full reality, which goes far beyond the Gary Vaynerchuk-tinted glamour of the late night “hustle”.

According to the US Bureau of Labor Statistics, 1 in 5 new businesses fail within the first two years, and whilst some of these may be due to external factors, as we have seen in the pandemic, or not having the right business skills or resources, the truth is that many of these businesses may have survived, had they known what they were truly heading into.

With this in mind, I decided to catalogue some of my most painful (and in some instances, painfully obvious) lessons from business — so far. Whether this causes new entrepreneurs to feel less embarrassed at similar experiences, or more experienced business veterans to shake their heads in nostalgia, I would love to hear your own experiences of the painful lessons you’ve learned in your early days in business.

1. Have a Support System — this may not be who you think it is

Friends and family are great; they love you and they mean well. But they also have a knack for saying just the wrong thing to derail your motivation train (which you probably spent all week trying to keep ON track) and send you spiralling into self-doubt and panic. Casual comments such as “Why don’t you get a real job too, just in case?” are often sprung upon you at reunions, and it can often feel like your work is seen as less valid because you don’t answer to an employer, even if instead you are juggling half a dozen clients.

When these moments happen, the primary coping method is to have your own internal comforting process: remind yourself that you know your work is valid, and that you are following your definition of success. However, there are also moments when it would mean the world to have someone else recognise your hard work and appreciate it. For those moments, it truly helps to turn to people who do what you do — whether that’s in the same industry, or simply also being self-employed — and know what it takes. This could be another family member, a former colleague, or even members of an industry-based Facebook group.

2. Be Fussy With Clients From The Start

When you’re first starting out, it’s natural to believe that you should be saying YES to anyone willing to hire you. After all, that is how you earn and learn, right? Perhaps, but this short term thinking is also a major trap that’s all too easy to fall into, if you don’t start with a clear idea of who your ideal client is.

When I first began freelancing, I decided I wanted to work with ethical brands created by People of Colour, who wanted me to help them grow a platform that they would use to address social issues. However, soon after I launched PIYA Media, I found myself approached by clients in a niche that I wasn’t passionate about. Not only did this make working with them less fulfilling, but it also meant that my portfolio started to grow in a direction that did not fully reflect my own brand. This is especially important when relying on word of mouth referrals from former clients to attract new business.

This does not mean that you should turn away good business. It does, however, mean that you need to look at your own messaging, and evaluate whether you’re positioning yourself in the right places and on the right platforms to attract your ideal client, before you find yourself only working with clients that don’t resonate with you, and wondering why you don’t have the time to pursue the clients you started out to help.

3. Set up a Backup System

Some days you’ll be ill, family emergencies will crop up, or technology will fail you. These are the days that you’ll need a little pre-prepared help.

Before any such emergency occurs, automate your work process, so that email templates, report templates, and anything else you can think of are almost ready to go. When you only have a fraction of time that you usually do, they’re a lifesaver!

Work out a set step-by-step workflow system for each of your tasks — you’ll be amazed by how much extra time, energy and mind space you have when you remove the constant decision making from your routines. It also makes training new employees much easier, further down the road.

And of course, make sure all of these templates and workflows are available (securely) online and offline, as you never know when you may not be able to access one or the other.

4. Time, Manner, Place

Yes, this is a German grammar rule, but it also applies here. It’s been vindicating to see how those less accustomed to working from home have adjusted to the same routines as those of us who do this full-time, and especially after past comments such as “It must be so easy for you to work at home in your pyjamas all day!” Now, I think there is a general appreciation that when working for yourself, discipline is the first and hardest rule to keep. Here’s a reminder of how to establish that discipline:

TIME: Get yourself into a routine, and calculate the time slots you have per week so that you can allocate tasks within this. Overbooking yourself is the fastest way to burn out or lose motivation.

MANNER: Establish a methodology to your work. Write it down. This will not only encourage you to stick to it, but will also come in helpful further down the line when expanding and hiring new staff, to maintain continuity and quality

PLACE: This is especially important while we work from home: many of us who did not work from home before Coronavirus have learned over the past few months how easy it is to slip into a habit of working in the same place that you relax, on the sofa or on (maybe even in) your bed. BIG mistake.


Your bed is not an office. Your sofa is not an office. Even your dining table is not an office — there’s nothing more frustrating than having to clear away your work, and with it, your thought process — in order to make space for dinner. Have a distinct area of your home in which you only do work, even if it is just a corner desk in a quieter room.

5. Be Your Own Boss…But Be Accountable To Someone

If you have a friend that also works from home, start the day off with sharing with each other what your goals for the day, or week, are. Then check in with each other towards the end of the day to see if you’re both sticking to your plan. This is a great way to take a quick break that’s also helpful to your motivation levels. For this to work though, you cannot break the following rules:

  1. Make sure you actually hold each other to account.

  2. Do not lie to your Accountability Partner

  3. Do not distract each other

6. Be Your Own Client

If you are a personal trainer, nobody will hire you if you don’t look like you keep in shape. Nobody will believe that you can produce the results that you know you can — and probably do regularly — for your clients. This applies in every industry; no matter how well you know your stuff, you need to walk the walk for yourself before anybody believes you can do it for others.

This is something I’m especially guilty of, so see this article as the start of me holding myself publicly accountable — check in weekly for new content! I’ll also be doing this across social media on Facebook, Instagram, Twitter, and LinkedIn, so be sure to say hi on each platform!